


Seven days of Valentine's

by Dadolorian



Series: SugarDaddy!Whiskey AU [2]
Category: Kingsman (Movies)
Genre: Aftercare, Biting, Choking, Creampie, DD LG, Daddy Kink, Dirty Talk, Established Relationship, F/M, Fingering, Fluff, Marking, Oral Sex, Over stimulation, Romance, Semi-Public Sex, Toys, Unprotected Sex, ex's mentioned, sadistic jack, use of safeword
Language: English
Status: In-Progress
Published: 2021-01-10
Updated: 2021-01-31
Packaged: 2021-03-14 01:27:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 27,680
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28663182
Author URL: https://archiveofourown.org/users/Dadolorian/pseuds/Dadolorian
Summary: Whiskey whisks his Sugar baby away for a romantic Valentine’s getaway.
Relationships: Jack | Whiskey (Kingsman) & Reader, Jack | Whiskey (Kingsman)/Reader, Jack | Whiskey (Kingsman)/You
Series: SugarDaddy!Whiskey AU [2]
Series URL: https://archiveofourown.org/series/2100495
Comments: 18
Kudos: 102





	1. Prince Charming

**Author's Note:**

> Thanks to @talesfromtheguild (Tumblr) for Beta reading and helping me with many ideas for this! 
> 
> This will be a weekly series leading up to Valentines Day
> 
> I try to keep Readers physical appearance as open as possible for this story, but please note in these chapters shes going to become more of a ‘character’, some specific interests of hers are going to come into play.  
> This is canon to the main Diamonds and Daddies story, but i am uploading as its own thing. You do not need to have read Diamonds and Daddies to read this, just know its a fic about Jack ‘Whiskey’ Daniels being a Sugar Daddy and the reader is a professional Sugar Baby.

_ Sunday 7th of February _

In your brief relationship, there was not a single morning you had awoken in Jack Daniels penthouse apartment without a smile on your face.

_ A week before Valentine's day was no exception.  _

As he tended to wake before you, Jack had many ways he loved to rouse you from your sleep, whether it be by making you breakfast and waiting until the enticing smell stirred you, or kissing you awake like some imagined Prince Charming. 

And he was, for you, he was perfect, a Prince Charming of your wildest dreams. 

He took care of you in every sense of the word - financially, physically, emotionally, sexually - it was by no means conventional, but the two of you couldn’t be happier. 

This was how he awakened you that week before your first Valentine's day together. His mustache and typical morning scruff tickled your neck as his strong arms wrapped around you, pulling your back flush to his front. 

He kissed his way across your neck, until he reached your jaw which received equal attention. You sleepily mewled and whined, always trying to chase your sleep despite how much you loved his affections, and despite how much you seemed to complain each morning, it did nothing to hide the smile on your face or make you desire waking up any other way apart from  _ this.  _

“I know you’re awake  _ Honey Bee _ ,” he rasped as he reached your lips.

It was slow, lazy, just your lips pushed up against each other until you began waking up enough to truly participate. His tongue pushed past your lips, not bothered at all by the morning breath, teased you, dancing his tongue around yours until you were moaning, finally awake and giving him your full attention. 

One kiss molded into another, and then another and soon enough the two of you had rolled into a more comfortable position for a lazy, early morning make out session. 

What surprised you about this particular morning was the fact that he pulled away just as your fingers raked through his hair in order to deepen the kiss further. 

Any day that started with a kiss like _ that  _ was usually followed by some hard loving by your cowboy Daddy. 

As he pulled away from you, rolling out of bed you gave him a confused pout, like a child who had her toy taken away. He simply chuckled at you and gave you a wink as he padded across his expansive bedroom naked to his ensuite. 

“Believe it or not Darlin, we’re on a schedule today and we need to be  _ up and at’em, _ ” he had called over his shoulder at you. 

Confused, you threw the soft bed sheets off of yourself and trotted after him, as bare as he was. 

“It’s  _ Sunday _ Jack,” you pointed out, he had promised you Friday when he had picked you up for Date Night that he had his whole weekend free for you. “You  _ promised.. _ .”

“I  _ know _ what I promised Princess,” he interrupted, warming up the shower as you entered the ensuite. “And that ain't changed. I just got something  _ special _ planned today, just for the two of us.” 

You couldn’t say you were surprised, Jack had turned out to be quite the hopeless romantic, taking you on surprise dates, or shopping sprees  _ ‘just because’  _ many times in the few months you had been an item. 

“Come on, let's clean up and get a move on. I can’t _ wait _ for you to see what I have planned.” 

  
  


* * *

A little over an hour later you were at home, Jack had sent you off with one of his drivers and the instruction to pack a small suitcase full of comfortable clothes for colder weather. That was the only hint you got as he fastened your seatbelt, gave you a kiss and sent you off. 

You sent him a few texts, asking him to clarify just what you would need, scared you wouldn’t pack enough, or too much, or forget something important. His phone was probably pinging every minute or so with your incessant questioning, but he wouldn't budge or give you  _ any _ hints. Instead he gave you a specific list of what you would need and promised should anything be missed, it would be taken care of. 

You returned to the driver waiting for you outside your apartment with everything Jack had asked you to pack, dressed in a warm, but stylish outfit so you wouldn’t freeze on whatever journey you were about to take.

You were expecting to head back to Jack’s penthouse, but instead, the driver started heading towards Brooklyn, away from Jack’s apartment. 

You had explicit trust in Jack and his driver, Blake, so you did not feel unsafe as you started heading away from home, you simply felt curious, and giddy over whatever Jack was surprising you with as you drove over the Brooklyn bridge. 

As you drove further into Brooklyn you pieced together where you were going pretty quickly, and your suspicions were confirmed when you finally pulled up to the JFK International Airport. You pulled your phone out to start texting Jack, asking where you were to meet you when the car continued past the drop off zone towards some rather serious looking security gates. 

Blake rolled down his window, giving the security guards whatever paperwork was necessary and continued on, driving you onto a runway and up to an expensive looking private jet where the man of the hour himself was waiting. 

Jack opened the door for you and helped you out of the car, ever the gentleman, placing a kiss on your hand as he did so. 

“Ready for your surprise Darlin?” He asked, chuckling at your confused but delighted expression. He had taken you on a spontaneous trip once before, for New Years Eve but only for the day, the two of you had barely flown far enough to join the mile high club together. But this time he had asked you to pack for  _ multiple _ days, the possibilities were making your imagination run wild.

“Where are we going?” You asked excitedly as your bag was loaded up and Jack led you to the jet’s stairs. 

“I told you,” he hummed playfully, squeezing your ass through your winter leggings as you boarded ahead of him. “It’s a  _ surprise _ .” 

With your persistent pestering you didn't even take in the surroundings of the opulent jet as you came in out of the cold. You continued to hammer Jack excitedly with questions as you were seated, but he stayed coy and secretive, not giving you even the slightest of hints no matter how much you batted your eyes at him and  _ promised _ to be his good girl. 

“No more questions Sweet thing,” he warned, silencing you with a tender kiss as you both strapped yourselves in. “This is a little treat just for the two of us, I got the  _ whole  _ week off to give you some good lovin and pamper you Baby.”    
  


You pouted up at him, sulking that he wouldn't tell you but  _ delighted  _ by the prospect all the same. A week, a whole  _ week _ alone with Jack in some far off place… He worked so hard it was rare to get a whole  _ weekend  _ with him, having only managed to do so a handful of times in the months he had been your Daddy. Sometimes even getting to see him after work was difficult, what with his spontaneous business trips. So to have another seven days of uninterrupted time together was a treat, and back just in time for…

You gasped. 

“Jack is this all for  _ Valentines _ ?” He didn’t answer, but his smile told you all you needed to know. 

  
  


Jack didn’t let you dwell on your destination too long once you took off, quickly distracting you once you were at cruising altitude with a luxurious inflight meal on par with any of the restaurants he took you to, the stunning view above the clouds rivaled the views of the city that you often were gifted on those dates. Lunch was followed up with Jack pulling you onto his lap on the plush sofa, attacking your neck in a flurry of kisses. 

“You wanna renew our membership for the mile high club Darlin?” he teased, nibbling on your ear. 

“Jack-” you sighed blissfully , whimpering at the growl he gave you in warning for the  _ incorrect name _ in the circumstance.  _ “Daddy,”  _ you continued, he rewarded you by continuing his kisses. “I wanna be a good girl for you but I don't wanna play in the bathroom again.” 

“Oh  _ Darlin _ ,” he rumbled hungrily, lips stilling against your neck and you felt his smile grow against your skin . “This jet’s got a  _ bed _ .” 

* * *

Jack had made sure the two of you had firmly reinstated your mile high club passes,  _ multiple times, _ within the remaining hours of your flight. Successfully distracting you and tiring you out to _ ‘help with the jet lag’ _ later. A  _ convenient excuse _ , you thought, but you weren't exactly complaining, you’d tumble into bed with him for  _ any _ excuse. 

He kept you in the dark still, even as you landed, he went through great efforts to keep your destination a secret. He had you sit in the private car on the runway as he dealt with a few security things, it was too dark and isolated from any noticeable landmarks for you to figure anything out from there, but as he joined you in the car he blindfolded you , had you put your earbuds in, took your phone and played some familiar music to  _ really _ make it difficult.

He kept you like that as you pulled up to what you could assume was your hotel, he led you inside, patting your hand in comfort as you clung to his arm, trusting him to guide you safely. 

Finally, when you arrived in what you could only guess was your hotel room, did he remove your blindfolds and buds. He smiled at you adoringly as he removed the soft silk scarf he had tied around your eyes, stepping to the side to allow you to explore and inspect your surroundings. 

It was a beautiful bedroom , modern, with a large walk in closet and ensuite to your left, to your right, a expansive bed with a small flatscreen TV mounted to the far right wall, there was a beautiful classical styled painting across it as a feature wall, and opposite the bed, a sliding door leading to the balcony. 

The only thing that could possibly beat the room itself was the _ view  _ from the balcony. You took a slow, cautious step towards the glass, gasping at the view, as nighttime lights lit up the coliseum opposite your room, making it sparkle. 

“ _ J-Jack _ , we’re in  _ Rome? _ ” You gasped, eyes watering as you were hit with a wave of emotion at the thought and  _ effort _ all of this had taken.

He came up behind you, wrapping his arms around your waist. 

“You said you always wanted to go,” he murmured in your ear, kisses trailing up and down your neck slowly. You had mentioned it once, in  _ passing, _ when the two of you had talked about traveling the last time he whisked you away. It had been a throw away comment as you both spoke about places you wanted to visit, you never expected him to really take note so early into your budding relationship. “Happy Valentine’s week  _ Honey Bee _ .” 

You turned in his embrace, smiling up at him as your tears escaped you.

You wanted to thank him, to express how damn thoughtful you found his surprise, how you adored him and everything he did for you. Words couldn't express those feelings well enough. 

“J-Jack, I-” 

“You don’t need to say anything Darlin,  _ I know _ ,” he said, still smiling down at you. He dipped his head to plant his lips on yours, it was the softest, most tender kiss he - no,  _ anyone _ had ever given you before, passionate and delicate at the same time, not the usual heated clashing of mouths you usually shared in the bedroom. He still tasted of the steak dinner -  _ lunch? _ \- he had on the plane. 

The time difference was a little disorientating, no wonder he had wanted to ‘tire you out’ on the plane. 

“Jack, what time is it now?” you asked in a whisper when you broke the kiss eventually. 

“Hmmm, here? Bout Midnight?” He answered. “Although back home it's about six in the evening. Why? I tire you out too much on the plane there  _ Honey Bee _ ?” He teased. 

“No,” you hummed, smiling. “I don’t think you tired me out  _ enough _ .” You took his large hand in yours and led him over to the bed. 

“Let me show you just how much I appreciate your surprise  _ Daddy _ .” 

  
  


* * *

The sound of chatter and traffic awoke you the next morning, it was rare you awoke before Jack, but with the excitement of the day before as well as the stress he was no doubt under trying to pull off your surprise, you were more than willing to let him sleep in, he had earned it after all. You untangled yourself from his arms as best you could to look at the time on your phone, 11:45 AM, much later than even you liked to sleep in. 

You were content to snuggle back up to Jack but the growling of your stomach compelled you out of bed, he complained in his sleep behind you at the loss of your heat as you rolled out of bed, but, you hadn't had dinner last night, given how late it was when you arrived, and you were  _ hungry.  _

You groaned as you threw on Jack's shirt from the previous day and padded off to explore the rest of your suite in search of food. 

The suite was impressively large, which did not surprise you, you knew Jack liked to throw his money around for you, he wouldn’t even think about cutting costs when it came to a special vacation for just the two of you. You found the lounge, it had a similar classical painting feature wall on one side of the room by the living area, one wall was all sliding doors leading to the balcony that ran the length of the entire room, giving you another stunning view of the coliseum. You could see people, tourists, walking about outside, you were eager to join their numbers, wanting to get out and explore, but not until after  _ food _ . 

On the other side of the room, past some soft red armchairs was a dining area, a modern looking glass table that could sit six people, beyond that was an equally modern kitchen area. 

_ Success. _

You didn’t really care about anything fancy to eat as you inspected the cupboards, a hotel like this no doubt had excellent room service but you were after something fast, something that filled your stomach and did not involve you trying to read or understand Italian and having to wait on delivery. You wanted it  _ now.  _

You settled on a generic looking brand of cereal, you had no idea what kind it was given it was, expectedly, in Italian. 

So there you stood, bowl in hand, in the middle of the kitchen as you ate your cereal. 

“I don’t like waking up alone _ Honey Bee _ ,” Jack’s raspy voice tickled your ear as he came up behind you, resting his hands on your hips. 

“I was hungry Jack” you mumbled around your spoon, not picking up on his tone of voice or use of your moniker. 

“If you were hungry  _ Honey Bee _ you could have just woken Daddy up and I would have happily given you a mouthful of-” 

“Jack stop!” You sorted trying not to choke on your cereal. “You’re  _ insaciable _ , you know that right? I lost _ count _ how many times we fucked yesterday.” 

“Can’t help it Darlin, can’t keep my hands off of ya,” he chuckled, kissing up your neck as his fingertips began tracing your thighs. “And who can blame me, with a body like this?” 

His fingers danced under the shirt you had stolen, further up your legs until he was back to your hips. 

“What have I told you before ‘bout underwear  _ Honey Bee _ ?” he asked, his voice dropping further, you picked up on his tone this time. 

“But _ Daddy _ !” You gasped, dropping into your submissive role easily. “I don’t know where our bags are. How can i put on fresh underwear when I don’t know where they are?” 

He hummed in thought for a moment, regarding your question. 

“Fine,” he said, removing his hands and slapping your ass playfully. “You got me there Honey Bee. But don’t let me catch you wandering about with no panties again,” he growled into your ear before pulling away. 

He moved around you to pour his own bowl of cereal. 

“Although, I don’t think you tried very hard to look for them  _ Honey Bee _ , because if you did you would have found them in the closet.” 

“Oh,” was all you could say, giving him a cheeky smile over the edge of your bowl as you drank the leftover milk. 

“Go clean up Baby,” he instructed as you put your bowl in the dishwasher. “I’ll join you soon, then we’ll go enjoy the rest of our day and see the sights.” 

  
  


* * *

True to his word as soon as you were washed and dressed in warm, comfortable clothes, some snug jeans, a stylish winter jacket and some waterproof walking boots, Jack took you out for lunch at a nearby cafe and then whisked you off to to see one of the many sights Rome had to offer.

He couldn’t book a room with a view of the famous Colosseum and  _ not _ take you there first. It was beautiful,  _ stunning _ , the February weather had covered everything with a soft blanket of snow, only adding to its beauty. 

You took some incredible photos together, you couldn't hide your giddy smile as you swiped through the large collection you had at the end of your tour of the colosseum. Jack was the first Daddy you had ever been with who was equally as excited as you to take photos together, your ex’s had tolerated your interest at best, flat out refused at worst. But each time you suggested a photo op with Jack he was equally as giddy as you as he pulled you in close for whatever photo you wanted to take. 

You giggled as you sent a couple off to your best friend back home, making sure they had a clear view of the Colosseum behind you. She was in for a surprise when she woke up. 

“Darlin, how bout we just wander the streets until we head back for dinner?” Jack suggested as the two of you were forced out of the Colosseum earlier than you would have liked due to closing hours. 

“That sounds nice, I haven't quite seen enough of Rome for today.” 

You walked hand and hand among the streets, window shopping, and actually shopping once or twice whenever you passed something that made your eyes light up in excitement, Jack was never able to deny you if there was something you _ really _ wanted. 

* * *

It was dark as you started making your way back to the Hotel, Jack carried your bags, insisted on it, a pair of shoes, a new dress, and a small collection of art history books you fell in love with. 

Your feet were sore as you unlocked your suite door and made it inside. You sighed in relief, ready to rest and warm up, order some room service as Jack had promised on your outing, and relax for the rest of the night. 

Jack had other plans it seemed, you were about to make a B-line for the living area when Jack stopped you in your tracks, pulling you in for a kiss and leaving you with an instruction to head to the bedroom. 

You gave him a curious look, noting how his tone wasn’t.. _.suggestive _ about the instruction. You turned and headed towards the bedroom, intrigued about what he could be planning. 

There, laid out on the bed, was a beautiful black lace cocktail dress, it hung off the shoulders and you  _ knew _ it would fit you perfectly. Next to it were a pair of black strappy heels, and two boxes. You picked the smaller of the two up, running your fingers over the black velvet covering it and opened it up. 

Inside was a stunning teardrop shaped necklace, matching earrings, and bracelet, you could only imagine what kind of stones they were, whatever they were, knowing Jack, they were _ real. _

You put the box down carefully and moved onto the other one, there was a handwritten note on top of it, you picked it up and were met with Jack’s messy scrawl. 

“ _ Day one of seven, Happy Valentine’s Week Darlin, Love Jack.”  _ _  
  
_

You placed the note on the bedside table and opened the larger box, sitting atop some delicate white tissue paper was a black strapless bra and matching lace panties, to match your dress. 

You smiled excitedly and rushed to change into your gifts. You no longer cared about your aching feet as you slipped on the heels, no longer cared about relaxing if it meant Jack had something in store for you. 

You tidied up your hair and touched up your makeup before admiring yourself in the mirror. He knew what suited you, the dress clung to your body, accentuating your best features, the heels made your legs look impossibly long and your new jewels sparkled, you looked a million bucks and you  _ knew _ Jack would love it. 

You sauntered into the now dark living area lit up only by the view outside, you leant against the doorway as your eyes landed on Jack, he was no longer wearing his outfit for the day, his hat, sunglasses, jeans, boots, flannel shirt and winter coat were all folded up neatly on the couch. Now, he was wearing a well fitted black suit as he leant over the dining table, that was laid out with a meal fit for a king, lighting some candles. 

“ _ When _ , did you manage to arrange all  _ this _ ?” You asked with an amused hum, pushing off of the door frame to join him.

He chuckled, shaking the match to kill the flame and turned to face you. 

“Darlin, I have this _ entire week  _ planned out to a  _ T _ ,” he smiled, pulling you towards him. His eyes wandered up and down your body as he rested a hand on your hip. 

“ _ Damn _ , I just _ knew _ you’d look gorgeous in that,” his hand ran up your side, admiring the way the dress fit you. “You liked your gift Darlin?” 

“I  _ love it _ Jack,” you smiled widely, cupping his face in your hands, giving him an adoring smile. “You know just what I like, what makes me feel sexy.” 

“You  _ are  _ sexy, no matter what you're wearing, but I have to admit, this dress just shows everything off _ perfectly _ .” 

You smiled bashfully under his compliments and stretched up to give him a peck to his lips.

“Now, dinner is served Darling,” he smiled charmingly, pulling away to hold a chair out for you.

“It smells amazing,” you said, sitting down, accepting his hand as you took your seat, he gave it a quick kiss before heading to a stereo to play some soft music. “What is it?” you asked when he joined you, sitting right next to you so you could both enjoy the view outside. 

“Can’t be in Italy without enjoying some pasta, now can we?” he smiled lifting the platter up to show you. He really did know you, having ordered you a dish that even though you knew you had never tasted before, you knew you would love from the smell alone. 

“I don't know how you do it,” you whispered, amazed. He cocked his eyebrow at you in question, asking you to continue. You picked up your fork and took a quick taste test, sighing in delight at the dish. 

“How do you know what I like before I do?” you finished. 

He smiled warmly at you, watching over steepled hands as you dug into your meal. 

“ ‘S my job Darlin,” he said, finally picking his own fork up to start eating. “I'm supposed to  _ take care _ of my girl...I pay attention to you.” 

“No ones ever really done that for me before,” you admitted quietly. 

“Well, you’ve had some shit Daddies in the past from what you’ve told me so far Darlin. Daddies who wanted to take more sugar from you than you could give, and weren’t willing to give back much in return.” 

You sighed dejectedly and nodded, agreeing with the sentiment. 

“ ‘S a good thing I came along, so I can give you everything you deserve,” he rumbled, leaning over to kiss your cheek. “You deserve the world and  _ more  _ Darlin.” 

His affectionate words brought a smile back to your face. “I don’t deserve  _ you _ ,” you hummed, giving him a kiss in return. 

“Darlin, I could sit here  _ all night _ trying to convince you that  _ I’m _ the one who don’t deserve  _ you _ ,” he laughed. “A man like me with the past I've had don’t deserve to be as happy as you make me. All I can do is try to make you even a  _ fraction  _ as happy as you make me in return.” 

Once again his thoughtfulness made you overcome with emotion, you felt your eyes tear up at his gentle words. Your lip wobbled as you kissed him again, thanking him silently. 

“You’re the best thing to ever happen to me,” you whispered, lips ghosting his as you pulled away. 

“ _ Ditto _ Darlin.” 

* * *

  
  


Jack backed you up into the bedroom, lips never leaving yours once dinner and dessert were done for the night. You wobbled, struggling to walk backwards in your strappy heels. Jack growled into the kiss, picking you up impatiently and continuing his strides. Your legs wrapped around his waist, securing you to his front as your fingers ran through his soft hair. 

He shoved the boxes that were left on the bed onto the floor before gently laying you atop the sheets. 

“Look so damn good in that baby,” he said huskily, eyes hungrily taking the sight of you stretched out in front of him. “But I'm afraid I need that off of ya now, need to know just how good those bra and panties look on you too.” 

You sat up and reached behind your back, carefully pulling down the zipper as you batted your eyelashes up at Jack who was shrugging his jacket off, his eyes never left your body. 

You shimmied out of the dress, tossing it to the side as you leant back and posed for him seductively. 

“I know whites my favorite color on you Darlin but i gotta say, you look sexy as hell in black,” he undid his tie and tossed it to the side, joining your dress. 

He began unbuttoning his shirt as you waited, watching _ him _ with just as much hunger. 

“You have good tastes Daddy,” you mewled as his shirt joined the other clothes. Your eyes raked up and down his torso, you  _ loved  _ how broad he was and his soft tummy, your gaze flew to his crotch as he began unbuckling his belt. He chuckled above you as you watched with a watering mouth, you licked your lips when he pulled his pants and briefs down and his throbbing cock was freed from his pants. 

“You wore  _ underwear  _ this time Daddy,” you gasped, surprised at the change. 

“Gotta keep you on your toes Darlin” he laughed, kicking his pants and shoes away.

“I didn’t know you even  _ owned _ any,” you teased with a giggle, laying flat on your back as he crawled over you. 

“Very funny,” he said, shutting you up with another kiss.

He lowered himself gently on top of you, making sure not to crush you with his weight as his tongue pushed past your lips. 

You both moaned in unison, his strong arms looped around your back and yours looped around his neck, molding the two of you together.

You felt his cock twitch against your clothed mound, rubbing against your clit slightly. Your moan turned into a whine at the slight stimulation. 

Your hips lifted up off of the bed to seek out more, one of his hands flew to your covered breast to tweak your nipple though the padded fabric. 

You had to push him away when you could no longer breathe, lungs starving for oxygen as you lay panting from the kiss and the stimulation his hand and rubbing cock were giving you. Jack didn’t want to break away, kissing down your front to your chest, giving you fresh love bights to lay his mark on you. Once his lips met the fabric of your new bra he moved to mouth at your neglected nipple through the material. You whined again at the added stimulation, arching your back to push your chest further into his mouth and hands attention. 

“Daddy  _ please _ ,” you panted, trying to chase more. 

He looked up at you, mouth not leaving you for a moment as he watched you watch _ him _ . 

“What do you need Baby?” He asked, sitting up. 

“More, I need  _ more, _ ” you whined, back arching further trying to chase the lost stimulation. 

“More?” He asked teasingly, slapping your thigh. “ _ Greedy girl _ .” 

You pouted at the admonishment, making him laugh. 

“Baby I should teach you a lesson bout being greedy, I spoiled you  _ rotten _ all day all day long and you still got the  _ nerve _ to demand  _ more _ of me,” he leant over to give you another kiss. 

“But,” he continued. “I really just wanna _ show you _ just how happy you make me, not just tell you.” 

He got up off of the bed and pulled you by your waist until your ass was resting over the edge. He knelt down on the floor, settling between your knees. 

“Can smell you Baby, smell how  _ wet _ you are for me,” he sighed, throwing your legs over his shoulders as he settled down more comfortably, hands on your waist holding you down firmly to keep you still. The heels were digging into his back slightly but he didn’t care, he had a thing for taking you with your heels on, he’d keep them on you as long as possible. He ran his nose up and down your covered slit, breathing in your scent and sighing in content. 

“Smells so damn  _ good _ , know you'll taste even better.” 

You whimpered at the feeling, trying to wriggle to push his face further into you but his grip on you held firm. 

His tongue flattened against you, licking up and down your panties until they were soaked by his saliva and your juices. 

He shoved his nose hard into your clit as he began lapping at your covered hole sighing in satisfaction at your taste as his eyes drifted closed.

He growled in warning at you, as you began to wriggle again, eyes cutting up at you fiercely. You sobbed, frustrated at his teasing. As good as his tongue felt it was  _ barely enough _ through the barrier of your underwear. You wanted to strip them off and toss them to the side, feel his tongue against your bare skin. 

“P-Please Daddy I-” 

He cut you off swirling his tongue around your clit, bringing one hand down so his finger could push up against your hole, teasing you. 

Your chest heaved, fingers gripping his hair tightly to pull his mouth closer to your clit. 

_ “Daaaaaaddddddyyyyy!”  _ You whined, trembling in his grip. 

He was watching you, fervently, committing every sound and image of your struggling body to memory. 

“I- I wanna cum Daddy,  _ please _ ”, you begged, fingers tightening in his hair. 

He shook his head.  _ No.  _

“Why Daddy?” You sobbed. “ I’ve been so _ good  _ today.” 

“I know you have Baby. Just hold out for me a little longer, this ain't a punishment,” he rasped, flicking his tongue over your clit, loving how the soaked fabric clung to every inch of you. “Daddy just wants to make this last. I promise I'll make you feel real good soon.” 

Your lip wobbled as you whimpered, trying to will yourself away from the edge.

“B-but it feels too good Daddy,  _ please.”  _

_ “Patience  _ Baby,” he gravelled , lapping furiously now at your clit. 

Tears fell from your eyes in fat drops, your body hummed in overwhelming pleasure as you fought against your body's reactions to his touches, trying not to cum without permission. 

When his mouth covered your mound and began sucking at your clit you let out a choked sob. 

“Daddy, please please please please  _ pppplllleeeeeaaaasssseee! _ ” 

“Allright baby, cum for me, cum for Daddy.” 

You cried out his name as the tension in your body seemed to snap like a wire as your orgasm washed over you. You clenched around  _ nothing _ as your body shook in his hold. 

“There we go, _ look at you _ Baby,” he cooed, unhooking your legs from his shoulders and standing up. You looked up at him with glassy eyes as you tried to come down from your high. He ran his hand over your soaked panties, showing you the mess that was coating his palm. 

“Look at that Baby, just soaked  _ right through  _ em. Don’t know how you’ll ever be able to get the smell out of em now.” 

He brought his soaked hand to his leaking dick, stroking himself to give himself some relief to his neglected cock. 

“You got another one in you Baby?” He asked, rubbing the tip of his cock into your stomach, wiping his precum onto your skin. 

You nodded up at him. 

“Course you do, my _ good girl _ , always got another one for me. Always hungry for my cock,” he rasped, releasing his cock to hook his fingers into your panties, pulling them down your legs , past your heels and tossing them over his shoulder. 

“There’s my  _ pretty little hole _ ,” he cooed, leaning down to give your now exposed clit a quick kiss. 

You gasped, still sensitive from your orgasm, just how he liked to take you. 

“Look at how  _ wet _ you are baby!” He said proudly, dancing his fingers over your tender lips. “I’m barely touching you, but I can _ hear  _ just how wet you are too, Daddy made quite the mess of you huh?” 

You shivered under his feather light touches. 

“Settle back on the bed however you want Baby,” he instructed, patting your thigh gently. “Then Daddy will give you his cock.” 

You repositioned yourself by the pillows, lying on your stomach, one leg higher than the other. You looked over your shoulder at him, eyes heavy lidded. 

“Ohh, my Baby’s  _ real _ tired today huh? He murmured gently, crawling back over you, cock twitching against your ass. “Made you walk around _ all day _ after a long flight, then made you dress up and walk about in heels. Did  _ so well _ . Allright. Let Daddy do all the work then Babygirl.” 

“W-what about you Daddy? Aren’t you tired?” You asked with a whine. “Maybe I should-” 

“Shhhh,” he silenced you gently. “Daddy is tired but I still want to take you, still want to  _ spoil _ you.”

He lined himself up with your pussy, gently pushing his hips forward. He moaned at the wet heat surrounding him, squeezing his dick. You wailed at the feeling of finally being filled. As satisfying as your orgasm was,  _ nothing  _ compared to being completely stretched and filled by Jack.

“There’s my perfect pussy. God, I  _ missed  _ this,” he groaned. 

“I-its only been  _ one night _ ,” you pointed out with a whimper. 

“ _ Too long _ Baby,” he growled in your ear before burying his face in your neck once he bottomed out. 

He started fucking you with deep, but gentle, slow thrusts, letting you feel every inch of him drag along your walls. The harsh stretch was aided by the copious amount of cum he had coaxed from you. 

He nipped and kissed at your neck as his arms looped around your stomach, holding you tight to his front, as if he was worried you might try to wriggle away. 

Wet, gentle trusts and your moans filled the otherwise silence of your room.

There was no desperate fucking, no pleading or dirty words, no hot and heavy slaps as his hips met yours. He took you carefully, gently, rocking his hips into yours. 

It was the most tender sex you had ever experienced, and for the second time that night your eyes teared up at the raw emotion it brought out in you. 

Even as his pace picked up, as he began chasing his relief, his thrusts remained gentle. A hand snaked its way down to you clit, circling it quickly. 

“B-Baby, cum, cum with me,” he pleaded in a whisper, hot in your ear. 

He held onto you tighter, groaning right in your ear as he reached his peak, pulling you over the edge with him. You felt his hot, thick cum fill you up as your walls fluttered around him, milking him dry of everything he had. One of your hands reached back to grip his hair, pulling him closer to your neck as you both moaned and rode out the aftershocks of your simultaneous orgasms. 

He continued to cling to you tightly as you both came down from your highs, letting your breathing return to normal and sweat soaked bodies cool. Eventually, he pulled out of you, rolling to his side but not letting go of you, spooning you. 

“Baby...You all right?” He asked, his hands tracing soft patterns into the skin of your hip. 

You nodded, sniffling as the tears that threatened to fall earlier finally broke free. Letting that tidal wave of emotion crash over you.

Jack lifted his head from the pillows, listening to your sniffles. “Woah, woah Baby! Why the tears?” he asked, pulling you closer to comfort you as he gently cupped your face and pulled you to look at him. 

“I’m  _ happy _ Jack, I _ promise _ ,” you laughed, even as your face was covered in tears. 

He sighed, shoulders relaxing as he looked down at you with a soft smile. “You had me  _ worried  _ Darlin,” he whispered, leaning forward to give you a gentle kiss. You could taste yourself on him mixed with the pasta sauce for dinner. 

“Come here, cuddle with me properly,” he said tenderly, helping you roll in his embrace so your head was resting on his chest. He kissed your forehead and stroked your hair, soothing you as you let your emotions roll free. 

“I’ve never..” you began, breaking the comfortable silence you had been sitting in, eyes focusing at the view of the Colosseum outside your room. 

“Never  _ what _ Darlin?” He asked, gently encouraging you to continue. 

“I’ve never had sex like that before, especially with a Daddy.”

“Like what? What do you mean Baby?” 

“Sex so _ gentle _ , so...tender. I got overwhelmed by how... _ emotional _ it was.” 

“Oh  _ Honey _ ,” he sighed sympathetically, kissing your forehead again. “You’ve really had some piece of shit Daddies in the past huh?” 

“Is that what making love feels like?” You asked quietly, Jack almost didn’t hear it. 

He froze for a moment, lifting his head to look at you. “No ones ever made love to you before?  _ At all? _ ” 

You shook your head no. 

He flopped back against the pillow with a sigh. 

“No, that’s not how _ I _ make love Honey...But I’ll show you...one day  _ soon _ .” 

The last thing you saw was the soft glow of the Colosseum as Jack’s steady heartbeat lulled you to sleep. “I’ll hold you to that,” you sighed, eyes drifting shut.


	2. Thank you's

**Summary for the Chapter:**

> Day two Jack takes reader to see her favorite work of art.

**Notes for the Chapter:**

> Thanks to @talesfromtheguild for Beta reading and helping me with many ideas for this!

_ Tuesday 9th of February _

__

The second morning in Rome started with an early morning makeout session, soft, gentle kisses roused you from sleep, followed by a shower and a traditional Italian breakfast delivered to your suite as the two of you sat watching people make their way to the coliseum. 

The coffee and crespelles were a perfect way to start the day, made all the more better by Jack’s large hand resting on your thigh, drawing gentle patterns with his thumb as you each sipped your mugs in comfortable silence. 

By eight thirty AM the two of you were dressed in your warm clothes and out the door, ready to partake in whatever adventure Jack had planned. 

* * *

You sat literally on the edge of your seat in excitement as you were driven around Rome to our destination for the day. Jack warmly chuckled beside you at your boundless enthusiasm, smiling wider to himself as you began snapping pictures along the way of the general beauty that was Rome. 

Once you were dropped off Jack took your hand in his, leading the way up the road and round the corner. You practically hummed in excitement beside him, bouncing in glee as the large walls of Vatican City loomed over you. 

  
“Jaaaacccckkkk!” you squealed delightedly, as he led you to the back of a growing queue. “Are we going where  _ I think _ we’re going?” 

He chuckled at your excitement again. “Couldn't take my girl to Rome without letting her see her favorite work of art could I?” 

You bounced in place, trying to express your excitement and gratitude in any articulate way you could, you cupped his face and pulled him down for an expressive kiss on his cheek. 

“You have no idea how excited I am Jack!” You elated, almost jumping for joy beside him. 

He tried to calm you down and keep you still by resting his hands on your hips, pulling you to his front in a gentle embrace. 

“I have a _ fair _ idea Sugar,” he hummed, kissing your brow affectionately. “I remember when you mentioned wanting to visit Rome, on our New Year's trip, just a passing comment, but your eyes lit up when you mentioned the Sistine Chapel, I just knew I had to take you one day Darlin.” 

Your hands rested lightly on his chest, with your gaze cast down you smiled, tenderly remembering the brief exchange you had shared months prior. At the time you never took much note of your conversation, having forgotten all about it until Jack had surprised you with this trip, but  _ clearly  _ Jack had taken notice, and went through great pains to make your wish you had barely ever shared before a reality. 

You had lost count of the amount of times he proved himself of how utterly perfect he was for you was incalculable. 

He amazed you every day, outdoing himself with each little surprise or adoring words, each grand gesture or gentle peck, each casual touch or passionate kiss.

Jack Daniels, as cocky, ridiculous, and flirtatious as he was, was _ everything  _ you had ever hoped for. 

“I wish I knew, just how to show my gratitude to you Jack,” you whispered softly to him.

He gently pulled your gaze back up to meet his.

“Darlin, you don’t need to do _ anything  _ other than stay with me. You’ve made this lonely heart feel something again for the first time in years, and that's  _ more _ than enough for me.” 

Your lower lip wobbled and your eyes threatened to spill, Jack preemptively stopped your sappy tears from spilling with a gentle kiss to your lips. 

“Come on Darlin, lines moving.” 

* * *

  
  
  


Jack walked arm in arm with you throughout the whole tour of Vatican city, your gaze was often fixed to the beautiful architecture or paintings, but everytime you glanced over at Jack, his eyes were fixed on you. You had his whole attention, not the paintings, not the tour guide,  _ you _ . 

“Jack?” You asked softly, concerned he was only humoring you and didn't actually care about anything you were seeing. “Aren't you interested in all this?”

“Oh I am Darlin,” he reassured. “But I love watching the way your eyes light up, better than any painting here.” 

“You’re just trying to butter me up Cowboy,” you smiled up at him. 

“Can’t help it Sugar, pretty thing like you on my arm? Who can blame me?” 

“You flatter me Jack, You’ve been sweet talking me from the moment we met, I don't even think you would know how to stop,” you teased. 

He chuckled and kissed your cheek. 

“No Darlin, I don't think I would know how to either.” 

It was impossible to express just how fantastical it felt to see some of the famous pieces found in the Vatican museum, Raphael’s ‘Transfiguration’, The statue of Laocoön and his sons, The Vision of St. Helen , Da Vinci's St. Jerome in Wilderness, masterpieces you had only ever seen photos of on the internet or in your meager collection of art History books.  _ Completely indescribable.  _ But these experiences  _ paled _ in comparison to seeing Michelangelo’s Creation of Adam, photos could not compare to how breathtaking it was. It loomed above you, alongside dozens of other High Renaissance masterpieces, but your eyes were pulled back to that one each time. 

You imagined Michelangelo, centuries ago, in his genius, laying on his back atop the precarious scaffolding as he painted it, how grueling it was, how long it took.

You never thought you would ever see it, not in person, it had been such a  _ fantasy _ to you you had never really mentioned it before until Jack had asked you those months ago.

Daddies had taken you on vacations before, trips to sunny beaches and tropical getaways, when they wanted to impress you and have you show some skin, but not once had they ever asked  _ you _ where you wanted to go, what _ you _ wanted to see. 

There had been no desire to share your interests, to take you to experience culture and art over bikinis and parties. Jack had been right, you  _ had  _ been with some shit Daddies before you met him. 

The picturesque beaches and clear oceans may have been pretty to look at, but it couldn't hold a candle to the beauty above you. 

Standing there, with your neck strained up at the ceiling, your eyes began to water for the umpteenth time since you had landed in Italy, but you willed them away this time, focusing on the painting to burn the experience into your memory and refusing to let the tears fog your vision as emotions overwhelmed you once again. 

“Baby?” Jack’s soft voice cut in, his arms wrapped around your middle as he came up behind you, kissing your forehead. “You good?”

“ _ Perfect _ Jack,” you whispered back, giving your neck a break by resting the back of your head on him. 

“Everything you ever dreamed about?” He asked, following your gaze to the painting.

“ _ Better, _ ” you sighed, squeezing his arms around you. 

* * *

  
  


You clung to Jack’s arm as you made your way out of Vatican city and back to the streets of Rome. He patted your hand affectionately, placing a kiss to your temple. 

You had been so, so...  _ moved _ , by Jack's surprise, by the artworks, by the experience and you knew you couldn’t express it to him. And you knew _ he knew _ .

You were beginning to understand the magnitude of his affections, he wasn’t just trying to  _ impress _ you, to show off and boost his ego like many men before him. 

No, Jack's masculinity wasn’t so fragile that he had to prove himself like that, he may flash his money for you, to buy you trinkets and clothes just as they  _ all  _ had before, but the way he went about it was so different. __

_ Stuff _ wasn’t what he relied on to keep you with him, no, he kept you by his side by paying attention, by  _ caring _ about you, for _ you _ .

He wanted to make you  _ happy _ , truly, and he expected nothing from you in return apart from your companionship. 

His words from earlier in the day were really starting to strike a chord with you.

_ “You’ve made this lonely heart feel something again for the first time in years.” _

You looked up at him from the corner of your eye as he led you through the streets. He seems to know where he wanted to go, and you trusted him not to get you lost. 

“Jack,” you whispered softly. “I-” 

“Don’t need to say a thing Baby,” he interrupted. “I know.” 

“But, I-” you sighed. “How?” 

“ _ How _ do I  _ know _ ?” he asked, amused. “Baby you thank me every damn time I do something for you, no matter how big or small, I've  _ picked up _ on a few things. I can  _ tell _ when you’re struggling to figure out _ how _ to thank me.” 

He stopped in his tracks, guiding you to his front and pulling one of your hands up to his lips to kiss it. 

“You tear up when something _ specially _ meaningful,  _ those _ are the times you can’t figure out what to say,” he cupped your face in his large, warm hands. They felt nice against the chill that had clung to your cheeks. “But you don’t  _ need  _ to say  _ anything _ Sugar, I can tell just by lookin at’cha you’re grateful. It made you happy, that's all I wanted. I don’t need a ‘ _ thank you _ ’, I just need  _ you. _ ” 

Your lip wobbled and you pouted up at him, making him chuckle. 

“See? Just like that, and I get yer waterworks running,” he teased, thumb wiping a tear that was threatening to spill.

You rolled your eyes and swatted his chest playfully. 

“ _ None _ of that Darlin” he laughed, ducking his head to kiss you. “My Baby gets all  _ sappy  _ for Daddy’s sweet words huh?”

“Don’t get _ cocky, _ ” you giggled, trying to duck from him gleefully. 

“Thought you liked me ‘cocky’,” he joked as you turned and tried to walk off, pulling you back into his grip, back flush against his front. “Specially when it’s inside-” 

“ _ Jack!  _ People are  _ watching! _ ” you laughed, swatting at him over your shoulder, grateful at least your conversation wasn't too loud and  _ probably _ not understood by the locals who rolled their eyes at the childish tourists as they passed. 

He laughed merrily, letting you go and gently taking your hand. 

“Such a  _ killjoy _ ,” he joked, leading the two of you again. “Come on then Sugar, lets get some lunch.”

* * *

Lunch turned out to be in this adorable local cafe hidden down many side streets. 

Jack told him a work colleague told him about the hidden gem, unknown to most tourists, and had made a point to bring you there. 

You sat inside, safe from the bitter cold as you sipped your hot drinks and shared croissants and muffins.

Silence passes between you, as you watch from your window the small trickle of locals walk by, trudging through the remaining snow slush, on their way to  _ wherever _ it was they were going. It was a perfect way to relax after your tour, Jack told you to enjoy it while it lasted, because he had one more surprise for the day. 

* * *

Jack’s _ second _ surprise was a tour of Castel sant'angelo. 

It was originally built as a mausoleum, over the centuries it became a fortress and castle, in modern times, it had become a museum. 

“Two museum tours in one day?” You asked, humming as the two of you walked over the beautifully sculpted bridge leading up to the impressive building hand in hand. 

“Well with it being so close to the Vatican, I thought  _ ‘Why not?’ _ , and I know how much my Baby appreciates her art and history,” he smiled.

Taking his words from earlier to hear, you thanked him with just a kiss on the cheek.

* * *

Jack  _ insisted _ the two of you could walk back to your hotel by the time you were kicked out of the castle at closing time. 

‘Just a forty minute walk’ he promised.

You pouted at him, shaking your head  _ no. _

“My feet are  _ killing me _ Jack,” you whined. 

“Won't it be romantic though Baby?” He asked, trying to convince you.“Walking through the streets of Rome at night? Just the two of us?” 

It did sound nice, in  _ theory _ , but the sky was clouded over, your feet hurt, the ground was covered in slush and it was starting to seep into your  _ supposedly _ waterproof boots. 

“My toes are going numb and it’s  _ freezing _ Jack!” 

“But Baby-”

“ _ Daddy _ ,” you sniveled, trying to appeal to his dominant, _ caring _ role over you. You wrapped your arms around yourself to block out the cold as the temperature dropped further. It was bearable in the day, sunlight and warm clothes enough to keep you reasonably warm. But you weren't dressed with the expectation of being outdoors too long, and as the snow began to fall you pulled yourself to his chest, snuggling into his warmth. 

“ _ Please _ Daddy, I don't want to walk like this.” 

He sighed and wrapped an arm around you, caving to his instincts to care for you. 

“Alright then, let me call a cab Honey Bee,” he relented, pulling out his phone. 

  
  


* * *

You groaned when you made your way into the hotel room, throwing the keycard on the table and collapsing by the door , tearing off your boots and letting your soaked, numb toes free. 

Jack chuckled at your dramatic behaviour, not removing any of his gear much to your confusion. 

“There’s a few more presents on the bed for you,” he smiled, heat in his eyes and flashing his canines at you as he crouched down in front of you, stroking your cheek. “Want you to go in there and put them on-” 

“ _ Jack, _ my feet are too sore for any heels toni-”

“No heels,  _ Honey Bee _ ,” he said, his tone and use of your moniker a clear warning for you to fall in line. “You’ll like it, I  _ promise _ . Now go open your presents and get dressed while I go pick up dinner.” 

He stood up as you nodded and took his hand when he offered it, helping you up and grabbing the keycard from where you discarded it.

“Be back soon Baby,” he smiled as he opened the door and left. 

  
  


Alone, you padded into the bedroom, your feet grateful for the plush carpet as you made your way over to the bed. 

Laid out across the sheets was a beautiful little pair of pink and black satin sleep shorts, a matching bralette, a cute pair of pink fluffy bunny slippers, and a long fuzzy pink gown. You ran your fingers over the material of them all, amazed at how soft they all were. 

Atop your outfit for the night was another folded up note. You picked it up carefully and opened it up, greeted by Jack’s familiar scrawl once again. 

“ _ Day two of seven, I know your feet must be real sore today Baby, I hope a relaxing evening with Daddy makes up for it. Get dressed and go pick out a movie out in the livin room for me.  _

_ Happy Valentine’s Week Sugar, Love Jack”  _

You softened, reading his words, again as you folded the note back up and began redressing. 

The satin felt even smoother as it covered your skin, and the fuzzy robe and slippers helped warm you up after your cold trip back to your suite. 

Once dressed you wandered out into the living area, delighted to see the couch covered in soft blankets and pillows, a gift hamper sat on the coffee table containing sweets, a bottle of wine, glasses and some foot lotion. Your heart warmed at the thoughtfulness of it all and how intimately comfortable it was.

As you snuggled under one of the blankets and flicked on the TV, scrolling through movie options you heard the keycard beep and the door unlock. 

“Back Darlin!” Jack called from the entranceway , you heard him put something down and head to the bedroom. 

He joined you a few minutes later, wearing nothing but a pair of sweatpants that hung low on his hips and his trademark stetson, carrying a large pizza box. 

You smiled and bit your lip, admiring his little tummy that you loved so much.

He placed the box on the coffee table and snuggled under the blanket with you. 

“Pick something out Baby?” He asked, one arm over the back of the couch and other hand wandering up your thigh under your robe and resting there. 

“I  _ think  _ so,” you hummed, relaxing back into his embrace and warmth, head resting on his shoulder. “Sci-Fi movie by the looks of it.” 

“ _ Prospect _ ?” Jack questioned. “Don’t usually sound like our kinda thing Darlin.” 

“Yeah, but one of the actors caught my eye in the preview clips,” you giggled. “He looks like you  _ Daddy. _ ” 

He quirked his eyebrow at you and gave you a shrug, letting you click play as he pulled the pizza and wine over for you to share. 

  
  


You almost choked on your pizza when the actor showed up and Jack exclaimed in annoyance that he looked nothing like him. 

“What are you _ talking _ about?” You laughed. “He could be your _ twin _ !” 

“I know for a  _ fact  _ my Mamma only gave birth to one Daniels boy thank you very much!” He proclaimed. 

You giggled hysterically, curling into him, trying not to knock the pizza box onto the floor. 

“He’s just you with more scruff!” You gasped for breath between your laughter. “Listen to him he’s even got a southern accent too!” 

“I resent being compared to a scruffy,  _ sweaty,  _ bastard space man who talks so damn  _ weird _ Darlin!” 

You covered your mouth, biting back a sassy comment about the ‘talks weird’ comment and tried to compose yourself. 

“How can you  _ not _ see it?” You asked when you finally calmed down. “The similarities are  _ scary _ .”

  
  


The two of you eventually agreed to disagree as you finished your pizza and wine and moved on to a few after dinner chocolates from the hamper. 

Jack rubbed your feet with the lotion as you lay on the couch sideways, easing the tension and soreness from your feet in his lap as the movie went on. You melted to his touch, unwinding from the long day on your feet. 

  
  


You had taken quite a _ liking _ to the southern spaceman with the silver tongue, much to Jack's growing annoyance, he grumbled as you cooed at the man on screen.

But as irritated as he was, he pulled you to his side in comfort as you watched your little crush have his arm amputated, hiding your face in Jack’s chest throughout the difficult scene. 

“ _ Poor Ezra, _ ” you murmured when the scene was over. 

Jack rolled his eyes and kissed the crown of your head. “I don’t know what you see in him Darlin.” 

“He’s your scoundrel, space-cowboy twin Jack. What’s not to like?” 

“Think you need your eyes checked Darlin. I might actually be bothered ‘bout your little infatuation if you didn’t insist so damn hard that he looked like me.” 

You giggled and settled down again against his bare chest.

“Hmm...”

“What are you  _ hmming _ about over there?”

“You’d look good with a little blonde patch.”

“ _ Shut up _ .”

  
  


When the credits rolled Jack switched off the TV, shrouding the room in darkness and stood up, gently pulling you up to your feet beside him. You were tired after such a long day, and the movie and snuggles afterwards only made you more tired.

He rested his hands on your hips and gave you a tender, soft kiss. 

“You like your new jammies Baby?” He asked, smiling when you nodded. “Yeah? You look so dang  _ cute _ in them.” 

He nuzzled his nose against yours. 

“Is my Baby too tired tonight? Or do you want to have some  _ playtime _ with Daddy before bed?”

You whined in response, resting your hands on his chest. 

“I _ always _ want to play with you Daddy.” 

“Oh I  _ know _ you do Baby, but Daddy thinks you need your rest.  _ Bed time _ for you I think.” 

“I don’t  _ want _ to go to bed Daddy.” 

“Think you’re awake enough for it Honey Bee?” he asked, gently shoving your new robe off of your shoulders and onto the floor. 

_ “Yes, _ ” you nodded. 

“Prove it,” he rasped, firmly pushing you to your knees in front of the couch and pulling his sweats down enough for his balls and hardening cock to hook over them. 

You licked your lips and looked up at him, taking him in your hand at the base. His eyes burned into yours as you opened your mouth and began kitten licking at his tip, circling your tongue around him.

You kissed him, from base to tip, worshipping his cock. 

He moaned at your teasing little touches and you felt him twitch in your hand, hardening slowly under your touch. 

‘That's it Baby, Get Daddy _ nice _ and hard,” he sighed, closing his eyes and leaning his head back to lose himself to the feeling of you coaxing his cock.

You felt the crotch of your sleep shorts become wet, aroused by his raspy voice and lewd moans. But you kept your hands where they were, on his thigh and cock, knowing if you touched yourself without permission his ‘playtime’ with you would become a ( _ delicious _ ) punishment. 

You relaxed your jaw and took him into your mouth, letting your tongue run along the underside of his length as you bobbed your head, taking him deeper into your mouth. 

He let out a loud guttural moan, hands cupping your head to keep you in place. 

“Hmmmmm  _ fuck _ Baby!” He spat, looking back down at you and gently thrusting his hips into your face, careful not to choke you. “You’ve gotten so good at that! Can take me so well now can’t cha? Almost all the way!” 

He rocked into you slowly, now fully erect in your mouth, you concentrated on breathing through your nose as he pushed himself deeper with each thrust. 

You had succeeded in taking him easier than when you first had gotten together, but it was still a struggle to truly deepthroat him and supress your gag reflex, so far you had never managed to take him all in before you backed out. You kept your hand on his thigh, ready to tap out when needed. 

Your eyes never left his face, and his never left your lips, watching as inch by inch his cock went further into your mouth. 

“ _ Breathe _ Baby,” he encouraged, hungrily watching his spit covered cock push and pull in and out of you. “If you can take me _ all _ the way in tonight Baby, I’ll give you a _ big _ reward.” 

You mewled around him, excited by his promise of a reward. He _ always _ delivered on those promises in a  _ spectacular  _ way. 

You took a deep breath through your nose and relaxed your throat as best you could, successfully taking him further, your jaw hurt and your throat protested as he pushed in even deeper. 

Your eyes watered as your lips finally met the groomed hair at his base. You blinked up at him, waiting for approval and praise for having taken him all the way for the first time triumphantly.

“Hnnng! Fuck! Good girl! Good Girl!” he panted, watching you, transfixed on the way his cock looked shoved all the way down your throat. “Perfect, warm wet little mouth  _ fuck _ !” 

He reached down cautiously, fingers tracing over your neck gently, feeling the bulge in your throat. You whined, feeling light headed as he gripped your neck and squeezed lightly, he gave an experimental thrust, even with the awkward angle and groaned at the feeling of his own hand squeezing your throat tighter around him. 

“Oh fuck Honey Bee I’m so _ deep _ ,” he moaned, squeezing tighter, making you more light headed. “Doin such a  _ good job _ , you need to tap out Sugar?” 

You shook your head no as best you could, head swimming and body buzzing as he chokes you with his hand and cock. 

“Can feel my fat cock moving inside you Baby, so damn _ hot _ , making me even fucking harder.” 

He kept thrusting into your throat slowly, careful to not actually choke you. You were getting a little high from the lack of oxygen, far more aroused by it than you ever thought you could be. You only tapped out when black dots started to swim in your vision. 

Jack pulled free without hesitation, crouching in front of you to check you were alright as the obstruction in your throat was gone and your lungs heaved in oxygen. 

You gulped down air hungrily as Jack kissed your face in praise. 

“Did so well baby, so  _ proud _ of you, you took me all the way,” he murmured, nose nuzzling along your hairline. He waited for you to be ready to continue , and when your breathing had calmed and you gave him a nod to continue, he kissed your forehead, stood up and pulled you to your feet with him. 

“As promised, my little girl deserves her reward,” he growled, nodding over to an armchair by the sliding door. “ _ Go sit _ ,” he ordered softly. 

You scrambled to comply, anticipating your reward with glee. 

He sauntered over, discarding his stetson on the coffee table before kneeling down in front of you, hooking his fingers into your sleep shorts. 

“Up,” he gently instructed, pulling them down your legs as you lifted your hips for him.

He brought the shorts up to his face and inhaled your scent, licking up the crotch of them to taste the juices that soaked them. 

“My baby tastes  _ so good _ ,” he praised, discarding the shorts over his shoulder. “Spread ‘em wide for me Sugar,” he said, gently coaxing your leg apart and licking his lips. 

He didn’t tease, intent on giving you your much deserved reward as he drank you down and shoved his tongue deep into your dripping hole. 

Your back arched, eyes closed and thighs shook, he pulled them over his shoulders to give himself more room, his strong arms wrapped around your thighs to hold them still.

You whimpered in delight, gripping his hair and pulling him deeper, his eyes cut up at you, letting you know that at any other time, an action would not be tolerated, and he would have you reprimanded for being  _ greedy.  _

But this was your reward, you deserved it. 

Jack did not hide his messy noises as he ate you out like a man  _ starved _ , wet smacks of his lips on your lower lips, the sound of his skin coming into contact with your dripping thighs, his moans and your sounds of pleasure filled the room. 

You gasped when you felt a thick finger prod at your hole, pushing up into you beside his tongue. Your head snapped down to watch as he slowly pumped his finger into you, his tongue began lapping up your folds until he reached your clit, suckling on it gently. 

“ _ Daddy! _ ” You whimpered, pushing your hips up further into his face. 

He gave you a cocky grin as a second finger joined the first, stretching you out so perfectly, his fingers were so much thicker than yours _ , fuck you loved his fingers so much _ , and he knew just where to stroke to make your body sing. In such a short time he had learnt your body better than you ever had. 

“My Baby wants to cum?” He asked, running his tongue over your folds again. 

“Yes,  _ please  _ Daddy,” you pleaded. 

“Daddy prefers when you’re patient Baby. But you earned it tonight,” he growled, standing up with his fingers still inside you. Your legs dropped from his shoulders as he leant over you to nibble at your ear, you felt your juices that still coating his jaw as his skin met yours.

He abandoned his slow pumps of his hand, fucking you hard and fast with his skilled fingers. You keened under him, writhing at the sudden change. 

“Look outside that window Baby,” he ordered in your ear hotly. “There's still people out and about, all they have to do is look up here, and they’d see you getting _ fucked _ by my hand.” 

You felt your core clench around his fingers at his words, a wave of your arousal flooding out, soaking his hand. 

“You like that idea Sugar? You like the idea of some stranger seeing my fingers buried in this pussy?”

You whimpered and tried to thrust up into his hand. 

_ “Answer the question! _ ” He growled.

“Y-Yes Daddy!” You cried, panting hard as you felt your pleasure building. 

“Yeah? You get off on the idea of someone else seeing you? Seeing what’s  _ mine _ ?”

He sucked a mark into your neck, hoping it would show tomorrow, his secret little claim. 

“Want everyone to see you? Like some kind of common  _ whore? _ You’re  _ mine Baby,  _ dont you forget that.” 

“T-that's what i want them to see!” You whined, racing towards the edge, hoping he wouldn’t deny you as he often did to tease. “I want them to see who-who I belong to!”

He growled in approval. 

“Yeah? What else Baby?” He asked, encouraging your line of thought. 

“W-want them to see...That you’re- you’re the _ only _ one who can make me cum, that you’re the only one  _ good enough _ !” 

“Oh Baby you sure know what to say to stroke your Daddy’s ego,” he hummed in pride. “Go on then, show them, show anyone watching how hard Daddy makes you cum.” 

You were already well on your way to your pleasure when he gave you permission to cum, but he helped you along by diving down and sucking  _ hard _ on your clit. 

Your back arched further as you screamed out his name, your walls clenching hard over his furious fingers, as they attacked that sweet deep spot inside you on a mission. 

It _ hurt _ how powerful your orgasm was, how hard his fingers fucked you through it. And as it washed over you you were ready for him to pull out, for him to let you come down from your high, but his fingers did not slow. 

You mewled, sensitive and sore from your first orgasm as you felt him forcing your body towards a second one already. 

“D-Daddy, too- too much!” You whined, wriggling in his grasp. 

“Yeah?” he asked, his teasing tone told you he didn’t believe you, he moved his head away from your clit to look you in the eyes, speeding up his fingers. “What’s your color then?”

Your hips began thrusting up to meet his hand again. 

“ _ Color  _ Baby?” He reminded. 

“ _ Green, _ ” bucking up hard now into his hand to chase your fast approaching second high. 

“ _ Thought so _ ,” he hummed, taking your nipple into his mouth through your bralette, gently sucking on it and tugging it with his teeth. 

When he had soaked the fabric and thoroughly teased you he released it.

“You’re going to cum again for me, _ that's _ your reward. Daddys going to make you cum so  _ hard  _ your pretty little pussy will be _ ruined  _ tomorrow.” 

You sobbed under him, anticipating how tantalisingly  _ sore _ you would be with great delight. 

“Come on, be a _ good _ little girl for me and  _ cum _ ,” he cooed, grabbing your jaw with his free hand to make you look at him, his face only inches away from yours. 

“Cum for Daddy, and I’ll fuck you right up against that window for  _ everyone _ to watch.” 

Your stomach flipped at the thought and your core tightened around his fingers again. 

“If it werent so damn cold out there I’d fuck you right on that balcony, so the whole of Rome can hear your screams for me.” 

He brushed your clit with his thumb as the words fell from his mouth, pushing you over the edge for a second time. 

“ _ That's it _ Baby, cum for  _ Daddy,”  _ he cooed softly, lips ghosting yours. “Squeezing my fingers so tight. Can't wait till my cocks all  _ snug _ up in there, my favorite,  _ perfect _ little hole.” 

His words made your second orgasm  _ just _ as powerful as the first, you shook hard in your chair and screamed loudly until your voice was hoarse. You tried to muffle the scream with your hands which, until now, had been gripping the armrest for dear life ever since Jack removed himself from between your legs. 

He was having none of that however, grabbing your wrists in his hand and pulling them away from your face to hear your screams of pleasure. 

He coaxed your orgasm as long as he could, slowing his fingers but still thrusting them hard inside you. Dragging it out.

You shook from the aftershocks each time his fingers shoved up against your cervix, whimpering as your breathing struggled to return to normal and body tried to unwind. 

He pulled his fingers free from you, loving how your pussy tried to suck them back inside. You mewled at the loss despite how oversensitive you were. 

He held up his hand to inspect it, proudly displaying how drenched it was in your cum. 

“Look at that Baby, down past _ the wrist _ ...You _ horny _ little thing,” he rasped, letting you watch as he wrapped his slick coated hand around his neglected cock, pumping it slowly, you could hear the wet pass of his hand with each pump.

“Stand up,” he ordered gently, not helping you as you stood up on shaky legs, struggling to comply as your legs threatened to give out underneath you. 

“Top needs to go too Honey Bee,” he instructed, watching you with predatory eyes as you raised your arms, taking the sexy little Bralette off and discarding it somewhere behind you. 

“Up against the window, arms up.” 

You wobbled over slowly, sighing as your body touched the cool glass. 

You felt so exposed up against the glass, despite the fact there was no one currently walking about outside, and there was no light in the living area now that the TV was off, the only light source being the lights outside, lighting up the coliseum. 

You could see Jack's reflection in the glass as he came up behind you, stepping out of his sweats. You could  _ hear _ him still pumping his cock with you slick.

Your back arched as he ran the tip of his cock over your dripping folds, making you gasp and shudder.

“Poor  _ Baby _ , still so  _ sensitive, _ ” he teased, pushing you against the cold glass with his free hand, making your nipples tighten painfully at the chill. You wriggled slightly as he pushed his hips forward, tip entering your hole. 

“Shhhh Baby, Daddy needs his fair share too, needs to fuck your pussy,” he sighed, your tight wet heat slowly enveloped him as he slowly inched his hips forward. 

“Need to make you cum.  _ One last time. _ ” He emethised the statement by snapping his hips forwards, filling you up completely as his hips slapped up against your ass. 

He gave your oversensetive body only a _ moment _ to adjust to the stretch before wrapping an arm around you and fucking into you hard and fast. His free arm grasped your neck, lightly choking you again as his cock hammered into you.

“Fuck, so  _ wet _ baby. Your cums _ soaking  _ me, _ dripping  _ down Daddys balls,” he rasped into your ear.

_ Slap. Slap. Slap. Slap. Slap, _ filled the room as you were shoved up against the glass with each thrust. 

You cried at the delicious stretch, at how he made your tender, sore hole buzz with pleasure every time he shoved himself inside, at how your body stung from the cold glass, and at the filth he rambled into your ear. 

“My perfect pussy, Daddy’s  _ pretty _ little princess. Think about how _ anyone _ could walk past. Could  _ see you, _ ” he teased, turning you on more. “Stuffed full of my cock, wouldn’t be hard, this low down, just need to turn their head a lil bit, ‘s all it would take to see you.” 

You moaned at his words, tightening around him. 

“Fuck, squeezing me so  _ tight _ ,” he whispered in awe,thrusting harder into you. 

You closed your eyes and lost yourself to the delirium of being fucked by him, trying hard not to cum around him until he gave you permission. 

He didn’t like it when you came without his permission.

He chuckled darkly into your ear, slowing his thrusts down to teasing rolls of the hips. “ _ There's someone now _ ,” he rasped, watching someone walk by further down the street, you cracked your eyes open and could see just how close they were, close enough that if you called out with the window open, they would hear. 

“I don’t think they’ve spotted us. Let’s see if we can change that shall we?” He suggested with another dark laugh, letting go of your neck to grip your hips with both hands, making it much easier to thrust inside you and leaving nothing to silence your noises as he slammed into you again with the same speed as before. 

You shrieked, watching with wide eyes at the passer by, hoping he did not hear.

It was annoying just how arousing the idea of this stranger catching the two of you was. 

Before you could even stop yourself, you came around Jack’s cock without warning. No build up, no tensing, it hit you so suddenly you couldn’t have stopped yourself if you had tried. 

He growled angrily behind you, pausing his thrusts as you squeezed him hard, as your walls fluttered and tried to milk his cock. 

There was no way you could hide what you just did, it may have snuck up on you fast but he _ felt _ it. Felt you squeeze him and shake in his grasp. 

“Did you just fucking _ cum _ Baby?” He snarled. “Without Daddy’s  _ permission _ ?” 

“I’m sorry!” you sobbed. “I didn’t mean to, it happened so fast!” 

“You got off to the thought of some stranger seeing you, isn’t that right?” 

“Yes, Daddy,” you whimpered pathetically, not wanting to anger him further by lying to him.

“Such a _ filthy _ little  _ slut _ ,” he berated, rocking back into you. “If Daddy didn’t need to cum so bad I'd punish you  _ right now _ . Throw you over my knee and remind you that  _ Daddy _ owns your orgasms.” 

“I know Daddy! I’m sorry! _ So sorry _ !” 

“I believe you Baby, but that don't change the rules. Doesn’t mean you get away without some sort of punishment.” He licked the shell of your ear, nibbling at you lightly. 

“Tomorrow night, I really  _ will  _ destroy your pussy. I’ll hold you down and fuck you so hard, till you cum so many times you  _ pass out _ , never letting up until you’re _ beggin _ me to. Daddy will choose how many times you cum, when you cum, and how  _ hard _ you cum, to remind you your pleasure belongs to _ me. _ ” 

You sniveled, panting as your breath fogged up the glass.

“ _ Y-Yes _ Daddy,” you agreed. 

“Now stay still, Daddy gonna  _ fill you up _ , get you nice and  _ creamy _ .”

His rocks built back up to the harsh thrusts, reserving no gentleness for you as his grip would no doubt leave bruises on your hips the next day. 

He growls, the steady slap of his thrusts, bumping of glass and the blood rushing in your ear was all you could hear. 

And even though you had already cum three times, you could feel a fourth bubbling deep inside, warming you up. 

He pounded you against the glass. 

He cursed as his thrusts became frenzied, violent bucks up against your ass as he chased his release. 

“Fuck, fuck, fuck, here it comes!” He bellowed, digging his teeth into your shoulder and marking you hard. He groaned against your skin as his hot cum flooded you. You felt it fill you and warm you up, even if he didn’t let you cum again, you adored the sensation of him filling you up each time.

His thrusts slowed as you felt his seed begin to leak out around his length. 

You mewled at the loss of the orgasm you knew he wouldn’t have given you anyway. 

He pulled out slowly, releasing your shoulder and watching as his softening length fell from you. 

Your knees buckled, but Jack was quick to catch you before you fell and scoop you up into his arms. 

“There we go Baby,” he murmured, gently nosing at your temple. “Let's get you sorted.”

As usual Jack’s aftercare consisted of his soft praises as he tended to your physical needs. 

He washed you, tended to your marks, dressed you back into your new pajamas, and tucked you into bed. You drifted in and out of his care, only catching a few words here and there. 

_ “Good girl”, “Did so well,” _ and “ _ So proud _ ,” were the familiar praises you heard.

He joined you under the warm blankets when he decided you had been thoroughly cared for, pulling you close to his chest to snuggle and murmur affections at you. You nuzzled deeper into his warmth, completely boneless and spent, listening to the gentle timbre of his voice as you drifted off. 

That night you dreamt about old castles and handsome southern princes. 

**Notes for the Chapter:**

> credit to @talesfromtheguild for this little bit 
> 
> “Hmm...”  
> “What are you hmming about over there?”  
> “You’d look good with a little blonde patch.”  
> “Shut up.”


	3. Punishment

**Summary for the Chapter:**

> Day three, Jack punishes his Honey Bee for disobeying his rules.

**Notes for the Chapter:**

> Thanks to @talesfromtheguild for Beta reading and helping me with many ideas for this!

_ Wednesday 10th of February _

“Where are we going today Jack?” You asked cheerily at breakfast as Jack placed your plate in front of you and warmly kissed your cheek. 

“You know I don't spoil your surprises Babygirl,” he chuckled, joining you at the table with his own plate. 

The pout you gave him only made him chuckle more. 

“Now don't get too bratty today Baby, you’re already in deep shit for tonight,” he teased, giving you a wink as he picked up his cup of coffee. “I’d hate to add more punishments, I'm not sure you’ll be able to handle what I have in store for you already.” 

_ Oh, _ you thought, _ that's a challenge.  _

* * *

It seemed Jack wanted to outdo himself each day, for that morning, after you left your suite he surprised you with a trip to Palazzo della Cancelleria, another museum, a palace built in the 1400’s that now housed an amazing Da Vinci tour. 

You were delighted, viewing the artistic masterpieces alongside iconic inventions and anatomical sketches. 

It felt surreal to walk beside such famous work. 

You were delighted as the two of you toured the magnificent building, taking photos here and there where you could. 

* * *

To follow up your tour of the palace, for lunch Jack had organized for the two of you to take part in a pasta cooking class. 

It was nice to step inside such a warm and inviting kitchen workshop, no need for the layers that kept you bundled up from the February chill. 

You were part of a small group of other tourists, mainly couples like you and Jack, but you highly doubted they shared anything close to the relationship dynamic you did. 

Remembering Jack’s warning from that morning, the one you had personally taken as a challenge put you in a playful mood. 

You didn’t want to make the other couples uncomfortable by being outright bratty for Jack, so as your cooking class started you began to tease him in a more subtle way. Subtle enough that no one would take notice of the interactions between the two of you and think anything was out of the norm unless they had a stringent eye. 

It started innocent enough, gently drawing patterns on his arm or thigh with your manicured nails while you sat listening to your instructor, or running your foot up and down his calf, simple little things any couple would do to one another affectionately when out together. But for the two of you, a simple gesture like that meant so much more when Jack gave you a questioning look, brow arched, his expression changed to one of fire and hunger when you gave him your innocent doe eyes, feigning innocence and naivety, he knew then what you were up to, and accepted your challenge. 

You stepped up the teasing once you were all allowed to head off to your work stations, while you would never intentionally flirt with anyone else out of your loyalty to Jack, you made a point to give one of the few single people in the class a polite smile as you passed, both you and Jack noticed the way the young man's eyes followed you to your station after the innocent greeting. You knew _ he knew _ you would never stray, that he felt secure in the relationship and didn’t see _ anyone  _ as a threat to what you shared. But what Jack was was possessive, and he often let you know he didn’t like anyone getting a taste of what was _ his.  _

Following close behind you, he tried to take your hand in his, a subtle way of showing his claim, but to further rile him up you gently pulled your hand out of his reach. You smiled proudly to yourself when you heard his soft growl of frustration. 

You were having tons of fun with the class on top of teasing Jack, squeezing him through his pant when no one was looking, gently pulling away from his affections, spilling a couple ingredients on yourself and making sure he was watching as you wiped yourself down, hand tracing your form in a way you knew would make him hungry for more. 

Your final defiant act that you knew secured further punishment that night was ignoring the warning he whispered in your ear, pulling away from him with a devilish giggle.

_ “You’re not the boss of me _ ,” you said in a cheery voice, as you all made your way over to the tables at the front of the workshop ready to eat your creations, you were smiling widely at the look he gave you in return. Hunger, frustration, rage and competition all mixed into one look. 

  
  


* * *

The second the two of you had finished your lunch and were out of the workshop Jack shoved one hand in your back pocket, pulling you close to his side. 

Your stomach flipped and you hummed in delight at the thought of just what Jack was going to do that night. 

You could tell by his mood he wanted to drag you back to the hotel and have his way with you, hell, you knew that if it wasn’t so cold he’d pull you into a hidden ally or nook to do the job there. You also knew Jack well enough to know he was enjoying your little game as much as you were despite his pretense of annoyance.

“Baby girl you’ve had  _ one _ warning already,” he grumbled. “If that class had been more private you would have already used up your warnings for the day.” 

You hummed again in response.

“It makes Daddy sick to his stomach to see you acting so proud of disappointing him,” in any other situation, his words might have actually caused pause, made you reconsider. He knew, even when you were in a bratty mood you did not like to disappoint him, but by the erection you had felt when teasing him his words rang hollow. 

“You’re damn lucky I had planned this day out in full, otherwise this next little treat of yours would be cancelled,” he continued. “ So don’t take this as a _ reward  _ for your little stunt at lunch.” 

You feigned innocence with a few bats of your eyes, making him moan in frustration.

“Don’t make me regret treating you today Darlin, be a good girl for me and-” 

“What's the point of being good for you if I’m getting punished anyway?” You asked, interrupting his warning. He cut his eyes to you, brow furrowed, silently reprimanding you for interrupting him. 

“I can promise you _ Honey Bee _ , if you don't behave for the rest of the day I will punish you so hard you’ll pass out,” he growled directly into your ear. You loved the tone his voice took on as he warned you, it became so much deeper and hungrier. 

“I thought you were going to do that _anyway_ _Daddy_?” You teased. “If that's what's waiting for me tonight, I might as well have some _fun_. It's hard to scare me with talk of more punishment you already promised will be intense.” 

He growled again, _ you had a point.  _

* * *

Your next treat for the day was a shopping spree at some expensive Rome boutiques. 

Jack grumbled at your cheery nature as you entered the first store, clearly frustrated at you as you continued to tease and reap the rewards of the day, acting like you didn’t have a care in the world as you tried on dress after dress for him. 

He truly loved to take you shopping, and as time passed he relaxed enough for it to feel like any other shopping trip, you could catch his eyes softening, smiling at you when you tried something on he had a particular fancy to, or wandering off, searching the racks to find whatever gem he knew would make you look  _ stunning _ . He had a knack for it, and he would smile proudly every time he presented you with something he had found and you would squeal in delight.

Occasionally you would tease, making that hunger flash in his eyes for a moment once again. Little things, comments like stating how a dress wouldn't allow you to wear underwear, or how one dress would be perfect to ride him in. 

He reminded you, each time you left a store with a new bag that this was not a reward for you, and that you were only making your punishment that night worse, and each time you flashed him a sweet little smile as if to say  _ I know, but I don’t care.  _

* * *

  
  


You had ended up with more bags of clothes, shoes and handbags than you honestly deserved after the teasing you gave Jack, and you had no doubt there would be plenty of retribution as you made your way to your suite. 

Jack unlocked the door and pointed you to the direction of your room following close behind to drop your bags into the closet to be packed away later. 

Just like the previous nights, there on the bed lay your gift for the evening. You bounced over to them excitedly. 

Laying out over the sheets was a beautiful soft, long sleeved knitted white dress. It was cute, and gave off that innocent air you know Jack loved. Beside it were a pair of white pumps, knitted tights and two white boxes, picking up the first one to open it, you confirmed it was another lingerie set. It was white, slightly frilly, and the material reminded you of the dress. Across the waistline of the panties and between the cups of the bra was a large white bow with a rhinestone heart in the middle. 

You lifted them out of the box to test the softness, you were surprised to find underneath, a second set. Sheer, frilly panties,with another bow, and a matching sheer, short babydoll dress, the set had no bra, and from just looking you knew Jack wanted you to wear that set during your punishment. 

The man of the hour came up behind you, wrapping his arms around your waist, fingers dancing over your stomach. 

“Almost didn’t pack them, was saving them for a punishment,” he explained. “Never expected to need them for this trip, but I’m glad i packed them just in case.” 

He began kissing at your neck, up to your ear. 

“You’ll look so good in that as I punish you Baby,” he teased. “Can’t tell you how long I’ve been saving that, waiting for the perfect day to have you wear it as I punish you, imagining you wearing that, with tears down your face as I  _ ruin _ you.” 

Your body warmed at his words and stomach tightened in knots. 

“Open the other,” he instructed.

Inside the second box was a small bullet vibrator with a wireless remote, your tightening stomach did a somersault looking at the toy you knew Jack had specific plans for. Tapped to the inside of the box list was the note you had come to expect. 

You ripped it off and opened it. 

There were two messages inside this time, his original message, he had written before he had decided to gift you with a punishment, crossed out but still legible, and his updated message. 

  
  


~~_ “Day three of seven, I hope you’re ready for more spoiling Darlin, Happy Valentine’s Week Darlin, Love Jack.’’ _ ~~

  
  


_ “Hope you’re now ready for your punishment tonight Darlin. Knowing you, you’ve decided to be a brat for the day knowing what's coming for you. And I know this is going to be the most intense session we’ve ever endured together Baby, don’t think I’ll go easy on you.  _

_ You best behave for the rest of this Valentines week- Love Daddy.’’ _

“Now, get dressed. We’re going out tonight” he ordered, smacking your ass as he turned back to the walk in wardrobe, presumably to go change too. 

You dressed in your new outfit, styling your hair in the mirror when Jack walked back in. 

He whistled low and long at the sight of you. 

“Damn Darlin, you really do look good in white,” he hummed, wrapping his arms around your waist again and kissing your cheek. 

“Looking good yourself cowboy,” you hummed back.

He was dressed in a look you could only describe as ‘casual fridays cowboy’. A black blazer style jacket, with a white t-shirt underneath, dark black jeans and black boots, to really pull the look together he wore his signature stetson, it was rare he ever went without it. 

“You forgot just one thing,” he said, leaving you for a moment to wander over to the bed. He picked up the vibrator and remote from their box and smiled wickedly back at you. 

You felt your panties dampen, eyes fixed on the toy as he came back. 

Standing behind you again, he placed the remote on the dresser in front of you both and lifted the hem of your dress with his free hand. Watching over your shoulder as his hand slipped under your tights and panties, pulling them forward enough to allow his other hand to sneak between your legs with the toy. It took a moment for him to find your hole with the tip of the toy from his position, but when he did he pushed it in slowly, teasing you and kissing your neck deeply on the mark he had inflicted the previous night. His mustache tickling your sensitive skin there. 

You moaned as the toy inched deeper inside you, then followed by his fingers as he pushed it as deep as it could possibly go. He thrust his fingers in a few times, shoving the toy against your sweet spot until you began to grow wet enough for your panties to be a slippery mess, before removing his fingers to your frustrated whine. 

He chuckled evilly to himself, bringing his now soaked fingers to his mouth for a taste. 

“Always taste so good Baby,” he sighed. “I can’t wait till we're back, then I can have my fill again, and again, and again.” 

* * *

It turns out you should have headed Jack's warnings, and that there  _ was _ something he could do to punish you further than what he had initially promised. 

You thought you could handle it, when he gently shoved the toy inside you earlier that night, that letting him have his revenge for your meager teasing wouldn't be so hard. 

It pays not to underestimate Jack you had come to learn.

You writhed in your seat as Jack edged you for the next couple of hours. Turning the remote on full blast and watching you trying not to squirm in the middle of the hotel's luxurious restaurant. 

You were thankful for the ‘romantic’ dim lighting and wine, hiding your flush somewhat and giving you a plausible excuse should anyone come close enough to notice. 

Jack held one of your hands in his, gently stroking your knuckles affectionately as the other hand in his pocket played with the speed of the vibrator inside you. 

Each time he brought you to the edge he’d turn it right down, chuckling at the glare you gave him each time. 

“Think of this as a lesson, practice to make sure what happened last night doesn’t happen again,” he teased , turning it back up all the way. 

“If I leave it on full, for the next five minutes, and you can hold out, if you can manage not to cum, you’ll get one reward tonight.” 

Desperate now for something, _ anything _ , that night, you agreed with a nod. 

It was torture, sitting there, panties, tights, and even the seat of your dress soaked though thanks to his teasing, resting on the edge of pleasure and willing your body so hard to not fall into it you couldn’t even pay attention to anything Jack was saying. 

The idea of provoking further punishment right now from him had you scared. You knew he would let you cum later, since he promised to make you cum so many times you’ll pass out, he wouldn't deny it to you as punishment, which only made your imagination run wild as to how he might further punish you should you continue disobeying him. Your thoughts were consumed by possible things he might do should you fail his little test. 

“Times up Darlin, good job,” Jack cooed eventually, cutting into your thoughts. 

You sighed in relief at that, but a small panic overtook you when you realized Jack wasn’t making a move to stop the toy or turn it down, he simply sat staring at you with a cocky grin as your body jolted, still trying not to cum without his permission. 

“D-daddy, please” you whimpered quietly. 

“Please  _ what  _ Darlin?” he asked, feigning ignorance. 

“Please, I don't want to disappoint you,” you bit your lip and tried not to rock your hips. 

“And you won’t” he hummed, leaning forward to grip your thigh under the table. 

“This isn’t fair Daddy,” you pouted. 

“Neither was teasing me all day Honey Bee,” Jack retorted. “Touching me, pulling away, riling me up with your dirty words. You brought this on yourself.” 

You whimpered, gripping your chair tightly as the toy buzzed inside you, knowing he was right. 

“Go ahead,” he whispered. “Cum, but if you cum now, Daddy’s going to give you a choice tonight, and you wont like it.” 

“W-will it be a punishment?” You asked through gritted teeth. 

He cocked his head, thinking about it. “Yes and no,” he hummed. “You’ll like either option, but you wont like having to choose just one.” 

That was enough for you, too desperate to cum at that point to really care about how vague his promise was, too far gone to care that it might be something you would dislike. 

“Cum for Daddy Baby,” he purred, watching in delight as you let yourself go in the middle of a public place. 

His hand was still on your thigh as you shook hard, trying desperately not to make a noise or thrash about, not wanting to cause a scene. 

You panted quietly, back bent and looking up at Jack as your walls fluttered hard around the toy. The fact that people could see you right now as you came only made you cum harder, you bit your lip to stifle any noises, but you could not hold back a long whine as Jack gripped your thigh tighter, encouraging you through your orgasm. 

You heaved air into your lungs as you came down from the high, Jack’s free hand came to gently brush some loose hair from where it clung to your sweaty forehead. He smiled at you softly. 

“Good job Baby,” he cooed, still not going for the remote.

You whimpered, body sensitive from your orgasm, and till buzzing from the toy inside you. 

“ _ D-Daddy, _ ” you pleaded. He watched you for a moment, felt you still tremble under his hand. 

“Alright Darl, we’re done here,” he said, finally reaching into his pocket to switch off the toy.

You sighed in relief, still breathing heavy as Jack stood up and offered you his hand, you took it and stood upon shaky legs. 

He had the meal charged to your room, so the two of you headed straight to the elevator to head back down to your suite. 

  
  
  


Jack stayed silent until the doors had closed and the two of you were alone finally. His strong arm pulled you in close, helping you balance on your wobbly leg and keeping you upright. 

“Did you like that?” He asked, whispering into your ear. “Did you like knowing that anyone could see you cum? Do you think they knew?” 

If it was possible for you to become any wetter than you already were his words would have made you so. As it was you had already soaked through everything but the seat of your dress, but you were well on the way to that as it was. Your thighs were slick, and the material of your tights made an obscene sound as they rubbed together. 

The doors opened to your floor and Jack took out the keycard from his pocket, unlocking the door to your suite. 

“You have exactly one minute to be in your second set and on that bed Honey Bee, legs spread ready for me” he warned as he closed the door and started taking off his boots. 

Terrified of disappointing him you took off, almost falling thanks to the boneless feeling of your legs and the white pumps you were wearing weren’t helping. You tore off what you were wearing the second you were in the room, not caring if you ripped anything as you tossed it all to the side and threw on the sheer dress and panties. 

You heard Jack put his boots away and pad over to the door, just in time as you laid down on the bed, flat on your back and legs spread for him. 

“There, you can be a good girl huh Dalin?” He cooed softly, shrugging off his blazer and letting it drop to the floor. 

“Don't you look good in that?” He said as he came up between your legs, stroking the smooth, wet skin of your thighs. 

“Like a pretty little doll.” He threw off his shirt and knelt down. “Daddy’s going to have so much _ fun  _ playing with his little toy tonight. Daddy might get a bit carried away though, might  _ break _ you.”

He reached up, squeezing your breasts through the material of your dress, making you gasp. 

“ ‘S like a fucking wet dream seeing you in that,” he rasped, rolling your nipples between his thumb and fore fingers, cooing at your soft whimpers. “I bought this on a business trip you know? Had photos of it saved on my phone, those lonely nights away from you, I'd stare at them, imagining you in it, jerking myself off to the thought of destroying you while you looked so delicate in this.” 

Arousal pooled out of you at his confession, imagining him at his hotel, panting your name as he pictured you dressed like this. You were soaking the fresh set of panties you had on, with how sheer the material was; it offered no protection to the sheets below you. It leaked out and pooled beneath you. 

Jack inhaled deeply, closing his eyes in satisfaction. 

“Can always tell how wet you are just from the smell baby. You’re dripping ain't cha?” He asked, one hand abandoning your breast to play with the mess you had created on the sheets. 

He moaned, feeling how wet you were. 

“Baby,” he sighed. “Love how wet you get.” 

He crawled up you to give you a deep kiss, letting his hand play with your clit through the barely there material. 

“You remember exactly what I promised for your punishment Sugar?” He asked, eyes blown wide and dark in arousal. 

_ Yes,  _ you nodded. 

“Tell me.” 

“You promised you would ruin my pussy. That you’d choose how times I’d cum, w-when i came, and how h-hard.” 

“That's right Baby,” he praised, kissing along your collarbone. “And you know what to say if you need me to stop right?” 

“R-red, or Yellow if I just need to pause.” 

“ _ Good _ ,” he said, rewarding you with one last soft kiss. “Cause once I start, nothing short of your safeword will make me stop till i think you’ve learnt your lesson.” 

You whimpered in a strange mix of fear, and arousal, excitement bubbled in your stomach as he nuzzled his nose down your front until he was nestled back between your legs, lifting the hem of your babydoll dress over his head. 

“What’s the most you’ve cum in one night Baby?” he asked, throwing your legs over his shoulders and pushed his nose up against your clit, slowly, teasingly licking up and down your slit. 

“T-three Daddy,” you answered, gasping at his teasing licks. 

“Just three?” he asked with a smug tone. “Was that my doin? Or some other Daddy manage to make you cum three times?”

“Y-you Daddy, you’ve made me cum the most in one night.” 

“Well then let's break that record then huh? I need you _ destroyed _ . Lets see if we can double it.”

“S-Six?” You asked agasp. You weren't sure you could manage that, but you were  _ more  _ than willing to try, for him. 

You gave him your nod of approval as you made yourself comfortable and he went back to licking the thin material covering your slit, growling at the taste of you.

He must have moved the remote for the vibe you had forgotten about to his jeans pocket, as he switched it on to its highest setting , making you back arch off the bed in a startled gasp. 

“Don’t you  _ dare _ cum till I say you can Honey Bee,” he warned, pushing the material of your panties aside with his fingers so one could enter your hole, pushing up against the base of the toy. 

His talented tongue circled your clit as the finger thrust inside you, jamming the toy up to your deepest spot over and over again. 

You saw stars, and bit back a loud moan as the vibe buzzed inside you.

It was almost too much to handle, but like in the restaurant you controlled yourself just enough to not fall into that precipice of pleasure until your Daddy gave you permission. 

You looked down at him, not surprised to find he was looking up with those blown out eyes. They were almost black with how wide his pupils were as he drank in your writhes and moans. 

“Fuck Baby, so hot,” he rasped before he began sucking on your clit,  _ hard.  _

_ “Oh! Oh! Oh! Oh! Daddy!” _ You wailed, gripping at the blankets as if your life depended on it, knuckles turning white. 

He growled, warning you not to cum without permission, making you sob in need and frustration. 

He shoved another finger up inside you, somehow managing to grip the base of the vibe, even coated in your slick. It began thrusting it in and out of you at a steady, even pace. Your back arched again, raising you up into more of his teasing mouth.

“Ohhhhh  _ Daddy! Please _ let me cum, _ please, please, please, please.”  _

“Come on then Baby, cum for me. Cum for your Daddy.” 

You shook, writhing on the bed, your core squeezing down around his fingers and buzzing toy hard. He kept sucking at your clit until you began leaking cum, abandoning your clit to drink up every last drop he could, even as you became too sensitive. You cried out at the feeling of his mouth lapping at you, wriggling hard as your body tried to get away from the overwhelming sensation. His free arm wrapped around your quaking thigh and held you down fast, and with no safeword falling from your mouth he refused to stop.

You weren't even given the chance to come down from your high as Jack pulled the toy from your still fluttering hole, growling as he watched it contracting around nothing. He tossed the toy to one side, forgotten and latched his mouth to you fully, drinking more of you down now that his hand was not in the way. 

You howled, tears falling from your eyes as his tongue shoved inside you as deep as it could go, drinking every drop of cum you gave him as if he was a man parched of thirst. 

You were confident it was two orgasms back to back, rather than one long, continuous one, but that didn’t matter, they blended together and wracked your body, leaving you a trembling, sobbing mess on Jack's tongue. 

Your body jerked with aftershocks when Jack finally had mercy on you, gently releasing you when he had had his fill of your cum. 

“ _ Delicious Princess _ ,” he groaned, standing up and wiping the mess you had made on his face off with the back of his hand and licking it back up, savoring the taste of you. 

“Was that one, or two times just then?” he asked, with a smug, cocky tone. 

“T-two, I think,” you wheezed, trying to bring your breathing back to normal and pull yourself back to reality. 

“You _ think _ ?” 

“T-two, it  _ was  _ two,” you affirmed. 

“Good,  _ good _ ,” he purred, crawling over you. He grabbed you forcefully by the back of your head to claim a kiss, you tasted yourself on him as he shoved his tongue past your lips, ravaging your mouth. 

He left your lips and peppered kisses along your jaw, down your neck and to your nipples, biting at them softly through the gauzy fabric. 

“That’s three down then Sugar, _ halfway there _ ,” he teased, whipping away what tears remained on your face, you wore his favorite mascara that evening, the one that made your tears jet black as you cried. 

“Pretty little thing,” he cooed softly, shifting to sit on the edge of the bed. “Come here Princess,” he ordered, taking your hand and manipulating your body into a position he liked, over his knees, erection digging into your stomach. 

“What's your color Honey Bee?” He asked, rubbing your leaking pussy through the material. You were so wet the thin material might as well not be there, for it felt like he was brushing up against your bare skin. 

“Green,” you confirmed with a determined breath. 

“Good,” he sighed softly, pushing the fabric to the side to shove two fingers back inside you. 

You let out a shuddering breath, trying to force your sensitive body to relax and try not to wriggle away. 

“I love how sensitive you get after you cum Darlin,” Jack praised gently, thrusting his fingers in and out slowly. “Can feel the way your pussy’s trying to pull me in, how it  _ quivers  _ under my touch.” 

His free arm looped around your middle, holding you down firmly, that should have told you he was about to start something intense, but you paid no attention until he asked you his next question.

“ _ So,  _ you _ liked _ trying to make me  _ jealous _ today?” He asked, voice no longer soft and gentle, instead it was deep, and hungry. 

You didn’t get a chance to answer as he sped up his hand, fucking you hard and fast with his fingers. The profane noises of his coated fingers thrusting into your hole filled the room, alongside your soft cries. 

“Answer the question,” Jack growled, hooking his fingers inside you to brush that sweet spot that had you crying out louder. 

“I-I just smiled at him!” You wailed, shaking in his grip, kicking your feet out to try break free. You knew what word would make it stop, but you refused to say it. 

“But you did it on _ purpose  _ Baby, I  _ know  _ you did,” he snarled, leaning over to speak directly into your ear, his breath was hot against you. “You weren’t just trying to be polite, you did it to make Daddy feel possessive, then you pulled away from him when he tried to take your hand. Well it _ worked _ , I took _ notice, _ and I'm going to remind you that you’re _ MINE _ , this _ pussy _ is  _ mine _ , your  _ pleasure _ is  _ mine _ , and if you  _ ever _ try that _ shit _ again, Daddy won't hesitate to take you right in front of whoever you're trying that shit on with. You hear me?” 

You nodded, weeping at the devastating pleasure that bordered on pain with how hypersensitive your body was and his words. 

You squeezed around his fingers, unashamedly aroused at just how possessive he could be over you. 

“You like that idea? Huh Baby?” He asked, taking notice of the way your fingers clamped down around him. 

“Y-yes!” You wailed. 

“I’ve learnt a lot bout you this trip Honey, didn’t realize how much you liked getting off to the idea of people seeing you. You got a little voyer kink there huh?” He teased. 

You shook your head no. 

“Don’t lie to me, the window, the restaurant, just now. You want people to see you don’t you? You want people to watch you get fucked!”

Again you shook your head no. “I-I want people to see how good my Daddy makes me feel!” You blubbered, bursting into more tears as you thought hard to keep from cumming again. It was amazing how quick he could bring you to the edge despite how sensitive you were. “I want everyone to k-know just how much I love Daddy’s cock!” 

He growled in approval, right in your ear. “You said something like that last night, made me so proud Baby.” 

He kissed your cheek before straightening back up. 

“For those sweet little words, Daddy's gonna let you cum again, come on, cum  _ right now.”  _

On command your pussy squeezed down hard, contracting around his fingers as he rammed them deep inside you. It ravaged your body just as powerful as the previous three had.

You were openly wailing as Jack pulled his fingers out from you, you heard him lap at them as he positioned you on the bed, on your back, ignoring your cries.

“Color?” 

“Green,” you answered, with little hesitation between your sobs. 

“Two more to go Baby,  _ almost there _ ,” he praised, lightly brushing his fingertips over your now swollen pussy lips. You shuddered, trying to curl in on yourself to protect against his touches. You did your best to ignore your body's instincts, and relaxed as best you could under his feather light strokes. 

“So _ sensitive _ , I love it,” he hummed. “You just want to crawl away, don’t cha? Hide from Daddys touches because your sweet little body can’t handle it?”

Without warning he shoved a finger back inside you, pushing the panties aside again. Your hand shot to his wrist on instinct, trying to push him away but he wasn’t having it, pushing deeper despite your body's protests. 

“ _ Ah ah Baby _ , I _ warned _ you,” he crooned. “ Nothing short of your safewords going to make me stop until I get _ all six  _ out of you.” 

He found your G-spot again, attacking it with talented fingers. Even though you wanted to keep trying you had little control over your body's natural instinct to push him away. You tried to push and claw him away, battering his chest or arm to try and escape the overwhelming sensation wracking your sensitive body. 

He held you down with a hand on your neck, hard enough to hold you in place and still allowing you to breathe somewhat comfortably. 

His hand dwarfed your throat, arousing you even more than you already were. 

“Look at you, sweet thing,” he cooed, mockingly. “Trying to wriggle away from me. Daddy’s not going to let you get away that easy. You’re going to lie there and  _ take it. _ ” 

You sniveled at how helpless you felt, lying there trapped in his grip, body being forced towards yet another orgasm you knew would be just as devastating as the last, it was painfully delicious torture and the control he had over your body was a constant turn on for you. 

“Please Daddy,” you whimpered, bottom lip trembling and fresh tears pooling in your eyes. 

_ “Please Daddy,”  _ he mocked with a deep, sadistic laugh, pulling his fingers free for a moment to slap your pussy, making you yelp and struggle harder. He sounded drunk on the power he had over you. 

His fingers dove back in and his hand sped up once more, you tried helplessly to claw at his wrist and pull him out of you, but he was so much stronger. He laughed again, taunting you for how pathetic your attempts were. 

“You’re going to cum for me, right now!” He snarled, dropping your throat to allow him to dive down and take your swollen clit between his teeth, biting gently and sucking hard. 

You screamed until your voice was hoarse, battering him with your hands as you tried to escape the cataclysmic mix of pain and ecstasy that shook your body.

You arched off the bed, white stars in your vision spreading out until everything went blank. 

  
  
  


Warm kisses peppering your face and gentle hands stroking your hair back roused you. Your eyes blinked open as you looked around the room confused until your eyes landed on the familiar face giving you those kisses. 

“J-Jack?” you asked, voice raw and scratchy. 

“Hey Baby, glad to have you back,” he murmured gently, nuzzling at your temple. 

“W-what happened?”

He chuckled softly, kissing your forehead. “I made you cum so hard you passed out, just like I promised I would.” 

“How long was I out?” 

“Barely a minute,” he uttered, kissing your lips gently. “You still green?”

You paused to pay attention to your body, you were still trembling slightly, you noticed, and you could feel that instinct to shy away from his touches still lingering, but even if your body was protesting, you were mentally still willing to continue on. 

“Yes,” you whispered with confidence. 

“Alright baby, one last thing. You remember at dinner, how I said you’d get a choice?” 

You nodded, curious as to what he had meant at the time.

“I’m letting you choose now...You can either cum on my cock, or have Daddy cum inside you.” 

Your eyes widened in surprise, mewling in complaint at the idea of only being able to have just one. 

“B-but Daddy-”

“No buts,” he interrupted. “I _ told _ you at dinner you wouldn’t like having to choose just one, but that's what you got for getting to cum then.” 

“W-where will you cum if i choose to cum on your cock Daddy?” You asked. 

“On your thigh,” he answered, making you moan in frustration. He knew how much you hated him cumming on your thigh, so close to where you wanted him, and so far away from the places you loved for him to mark you with his seed, if for whatever reason he chose not to fuck your holes, like your face or breasts. 

You thought for a moment, agonizing over the decision, you wanted both, as sensitive as you were, you were always eager for his cock, it filled you up in a way nothing else ever could, to cum around him beat every other sexual experience you ever had. But you also loved the feeling of him filling you up, claiming you in a way he had not allowed himself the pleasure of experiencing for many years before he met you. You knew you were the only woman alive he had claimed in such a way, the only one he had cum in without a barrier,and each time he filled you up that thought rested in the back of your mind, reminding you you were  _ his.  _

You wanted both, but to have him claim you, to cum inside you, reaffirming what you were to him, that was far more important to you now.

“I-I want Daddy's cum,” you sighed resolutely. 

He smiled and kissed your lips softly. “Then you’ll get Daddy's cum, but you still owe me one more orgasm.” 

He settled down beside you, pulling you close to his side with one arm, holding you tightly. His free hand danced down your body, he chuckled as your skin jumped under his touch, still too sensitive. He brought his hand between your legs, teasing your entrance with the tip of his middle finger as the heel of his palm rubbed against your clit, your slick coating his skin. 

Jack kissed your temple as you whimpered and wriggled slightly. 

“One more Princess,  _ you got this _ ,” he encouraged. “Then Daddy's going to fill up your sweet little pussy, fill you up with my cum.” 

You nodded, encouraged by his words as his finger pushed in, agonizingly slowly. 

You cried out softly, voice too wrecked for anything above a faint whisper. 

“How shall i do this?” He asked, voice light and teasing. “Fast or slow? Do I drag this out until you wail for me again? Or do Fuck you so hard and fast you won’t know what hit you?”

“Y-you’re  _ mean _ Daddy,” you breathed. 

“Only sometimes Darlin,” he said with a devilish laugh. “Now, hold on tight, Daddy wants to feel this snug little pussy wrapped around his fat cock sooner rather than later. Daddy's cock feels neglected, needs some of your sweet sugar. ” 

He started thrusting his finger into you hard yet again, rubbing at your clit with his thumb rapidly thanks to the copious slick and cum that still coated you. 

“Daddy loves the sound of his fingers in your wet little pussy,” he teased, competley ignoring the way your body reacted to the sudden, vicious finger fucking as he had the last time. 

Again you shoved at him, batted at him but he continued to hold you tight.

You sobbed and shook, trying desperately to twist from his embrace. 

It felt good,  _ so good _ but your body was struggling to cope with the overstimulation. 

It was too much,  _ far _ too much, and you had clearly overestimated how ready your body was after passing out from pleasure. 

You were willing, but your body seemed to have other plans. 

_ “Yellow!”  _

Immediately Jack stopped, freezing completely as you panted hard, he didn’t pull out, understanding your cry was for a pause, not for him to stop completely. 

He waited patiently for you, not questioning you at all as he waited for your call. 

“I-I’m sorry-” you started after your body had relaxed enough for a coherent thought. 

“Don’t be,” he interrupted firmly. “Don’t _ ever  _ feel guilty or sorry for having to use your word Baby, there there for you, and i aint ever going to be disappointed when you use 'em.” 

He kissed your temple again. 

“What do you need?” he asked. “Need me out?”

You shook your head no. 

“I want to finish this, i don't want to leave you-” 

“Don’t,” he interrupted again. “My job is to take care of you, and if it gets too much for you, I’m  _ more _ than willing to ignore my needs and pleasure in favor of taking care of my girl.” 

You smiled softly at that, grateful once again for the seriousness he took in his role.

“I still want to though,” you whispered hoarsely.

“Okay then,” he sighed. “If that's what you want, just take all the time you need Sugar.” 

You weren't sure how long it took for your body to come down enough for you to feel comfortable continuing. Jack laid beside you the whole time, not a single complaint leaving his mouth about having to wait, and he was careful not to agitate your sensitive body by moving his fingers too much, even when his arm began to cramp up. 

Some indeterminable time later you nodded at him, giving the go ahead. 

“Green,” you whispered. 

Jack kissed your lips tenderly, before testing you with one gentle thrust of his finger. 

You whimpered, but reaffirmed your color was still green for him, encouraging him to pick up the pace. 

He watched your face carefully, as his pace slowly increased and you clung to him, he whispered soft words of encouragement in your ear as he built you back up, taking you right to the edge of pleasure. Rubbing at your swollen bud with the pad of his thumb gently.

Skilled, thick fingers hooking inside you again and stroking at your G-spot, expertly manipulating your spent body towards your final orgasm.

He coaxed you over the edge gently. Softly ordering you to cum for him with a whisper in your ear.

Your last orgasm wasn’t as strong as the others he had given you that night, your body far too overstimulated to manage anything as powerful as that. 

It still shook your body, and your walls contracted slowly, weakly, painfully and spectacularly around his finger.

Once again he reaffirmed your color was green as he moved to hover over you, unbuckling his belt with one hand and shoving his pants down just enough to free his cock. 

“Fuck Baby I _ need _ you,” he panted gently shoving your legs apart with his thighs as he nestled between them, rubbing the tip of his cock up and down your folds just enough to gather your slick. 

“Feels like i’ve been hard for  _ hours _ , need to cum so bad, watching you cum, so fucking georgeous, so sexy.” he murmured, pushing his throbbing cock in slowly. You whimpered but did not struggle, body finally too spent to do anything other than cling to him. 

“Fuck, I ain't gonna last Darlin,” he panted, immediately thrusting into you slowly, he was holding back, not wanting to torture you any further. His length dragged up against your sensitive walls, feeling them quiver around him softly. 

It was less than a minute when he began thrusting harder into you, unwillingly ignoring his desire to be gentle to you, chasing his own release with reckless abandon, lost to the feeling of your swollen and sore pussy squeezing him. Heavy slaps of his hips meeting your slick skin filled the room followed by his increasing grunts and curses. 

“So wet and tight, my perfect little pussy,” you heard him ramble to himself. “Watching you cum, so fucking hot. Like my own private porno. And that little dress,  _ fuck, _ Look so sweet an innocent, and your tits look so good.” 

You moaned, sensitive, sore, but loving the way he filled you, even if you didn’t get to cum again, you savored the feeling of him inside you, you doubted your spent body wouldn’t have been able to get there anyway.

Having him inside you, about to fill you up was more than enough for you.

He cursed, over and over again as he chased that high, needing one final thing to push him over the edge. Needing your encoragment. 

“Fill me up Daddy,” you begged in a whisper. 

That was all he needed as he began slamming into you desperately, groaning loud right in your ear as he filled you up with hot cum. You held onto him tighter, feeling his taunt, sweaty muscles flex and move under your hand as he thrusted in deep one last time.

It  _ felt  _ like it was never ending, that he came inside you multiple times, enough for it to pool out of you and onto the sheets, you imagined it, ruining the sheets you had already made your own mess on earlier. 

The two of you groaned in unison, clinging to each other as you both wound down.

With extreme care Jack pulled out of you, moaning at the sight of your combined releases leaking out of you. He wanted to push his cum back in, but didn’t want to agitate your body any further. 

He kissed you tenderly as he stood up, sauntering off with a satisfied sigh to do what you assumed was his usual after care routine. 

You didn't hear the bath turn on in the ensuite.

When he returned to your side Jack gently picked you up bridal style, cooing his usual soft words at you as you gave a confused whine, carrying you to the ensuite where you took notice of the bath finally. 

He helped you undress and assisted you gently into the bubbles before scooting in behind you, holding you to his front affectionately. 

You lay there, safe in his arms, relaxing with him, he murmured words of affirmation, praise and devotion into your ear as he held you. And when it was starting to get cold he helped you wash your hair, massaging your scalp as you had shown him how to do not that long ago with the shampoo as you melted to his touch. 

Tenderly he washed your body with your favorite body wash, being careful of your sensitive sex as he washed between your legs. 

When the two of you were washed and relaxed, he helped you back out and wrapped a large fluffy towel around you, drying you off just as delicately as he had been when washing you. He then helped you with your hair routine, doing as you instructed and making sure it was dry and ready for bed as he dressed you in the t-shirt he had worn under his blazer, knowing how much you loved smelling him when you needed to ground yourself. 

He dressed in sweats and carried you back to bed, holding you gently in his arms as he praised you softly for your efforts that night, allowing you both to recover from such an intense session, both physically and mentally for the two of you.

He made sure you knew just how proud he was of you, how much he cared for you and wanted to make you happy, as you drifted off, you repeated his words back to him. 

  
  
  
  
  
  
  
  



	4. Presents

**Summary for the Chapter:**

> Day four, Jack gift Honey Bee a special gift.

**Notes for the Chapter:**

> Thanks to @talesfromtheguild for Beta reading and helping me with many ideas for this!  
> This will be a weekly series leading up to Valentines Day

_ Thursday 12th of February _

As promised, you were left with a very sore and tender pussy. 

You awoke in uncomfortable pleasure with Jack's face buried between your legs, devouring you as if he hadn’t had his fill of you less than eight hours earlier. 

Lazily, you tried to push him away with your hand, in a feeble attempt to fall back to sleep, however thanks to your lingering sensitivity and the skill of his tongue he managed to coax you to orgasm despite your meager attempt to recede back into sleep.

You whimpered, grogginess clear in your high whines, as Jack lapped you up, savoring your taste before beginning to kiss his way up your body, pushing up his t-shirt you still wore to kiss at more of your soft skin. He gravitated towards your lips finally, lazily melding his mouth to yours. You tasted yourself on his tongue, alongside that taste you couldn’t describe as anything other than Jack. You moaned together, as if relieved to be connected once again finally.

Strong, familiar arms wrapped around you and lifted your hips to his, he hissed into your kiss as your soaked core rubbed up against his erection through his sweatpants.

“Is your sore pussy up to taking Daddy this morning?” he asked when you finally separated your lips from one another. His voice was raspy with sleep and need.

“If I'm not too sensitive for you to eat me out before I’ve even woken up, then I’m sure I can take your cock  _ Daddy _ ,” you cooed, giggling at the way his eyes darkened and the hungry look he gave you as he quickly hooked his sweats under his cock and balls.

“If you can still take me after last night, then clearly I didn't do a good enough job,” he teased before he pushed himself inside you with a satisfied groan.

* * *

  
  


Even with Jack’s morning distraction he had the two of you out the door, before noon, dressed ready in warmer clothes than usual due to the reported snowfall.

He took you to Piazza Navona, it was beautiful, even with the overcast gray sky, thanks to the cold February air it was not as busy as you expected, giving you and Jack plenty of space to roam about the decadent square to observe the beauty of the architecture and fountains.

Snow covered the ground, which did not dampen your experience in the slightest. Jack promised to ‘make up for it’ in the future by taking you back in warmer months, but you silenced his worries with a kiss. 

“I am  _ thrilled _ we are here, even if it's cold, I don't need blue skies and sunshine to appreciate  _ any _ of this Jack.” 

He gave you a soft smile in return, feeling some of his worry lift.

“I still want to take you back here Sugar, one day.” 

“I would _ love  _ that, I just don't want you thinking I'm somehow disappointed because you took me here in late winter. I love it Jack,  _ thank you. _ ” 

You shared a deep kiss in front of one of the fountains, as the only two people in the square. 

* * *

You were equally as excited when Jack took you to your next location for the day, and found it was just as empty as Piazza Navona. Trevi fountain was covered in snow, the blanket was growing steadily thicker as snow began to fall, Jack was grateful he had the foresight of an umbrella that day, opening it up and pulling you to his side as you both made your way over to the famed fountain.

“This is amazing, that we get to experience such a place, just the two of us” you whispered, leaning your head on his shoulder, huddling closer to him against the cold.

“It seems surreal Darlin,” he hummed beside you, kissing the crown of your head. “It’s like we’re the only two people in the world.”

You giggled. “Hmmm, and is this what we would do? If we were? Travel around, seeing the sights?” 

“If it were just the two if us, I would want nothing more than just to explore the rest of the world with you, Honey Bee,” he smiled. 

* * *

You flipped through photos you had taken that morning on your phone as you sat in the passenger seat, Jack beside you holding your free hand as the driver took you to wherever he had planned for your lunch. 

You giggled at one particular photo, Jack was pulling a face into the camera as he would often do when in a playful mood.

“Send me them when you get a chance Darlin,” he said warmly beside you, smiling at your smile. You gave him a nod before swiping through more. 

* * *

Lunch, as it turned out, was very similar to yesterday's lunch, as Jack had surprised you with another workshop. However,  _ this _ time you were taking a pizza class. 

Your stomach growled as you entered the warm Pizzeria, shrugging off the thick winter coats you wore and hanging them up. You were grateful for the change in temperature as you both cleaned off the snow clinging to the rest of your clothes before joining the small class. 

You decided to spend the time this lesson enjoying the experience more than teasing Jack, who seemed just as agreeable to the notion as you stood side by side at your station, listening to your instructor. 

You had a lot of fun, Jack kneaded the dough for you as you stood to the side, admiring his arms as he rolled up his sleeve and got to work. As the dough was stored away to rise, you cleaned your station together, sitting down to decide what toppings you each wanted. 

Your pizza base was an uneven circle, Jack rolling it out once they were all deemed acceptable. You giggled at the lopsidedness of it, taking a quick photo of Jack’s pout as you giggled over your lumpy pizza base. 

Together you made the sauce and spread it on your base, before you were finally allowed to decorate it with toppings. Before you could start, Jack made an equally uneven heart shape out of your shredded mozzarella, and with sauce bottle in hand, he managed to write a very messy “JD ❤️ HB” 

You ‘awwed’ at the gesture, quickly snapping a picture of Jack next to his creation, smiling proudly. 

“How very ‘cheesy’ of you,” you joked lamley, making Jack groan.

You finished putting the rest of your toppings on before you were finally allowed to deliver your pizza to the pizza oven. Jack was thrilled to get to use the large wooden pizza peel, and you made sure to take a video of Jack putting your pizza in the large oven to cook with help from the instructor. 

While your lunch cooked you cleaned everything up, leaving your station as spotless as you found it. When the food was ready you and Jack sat at the tables, alongside other couples, chatting away happily as you all ate together, his arm around you lazily. 

* * *

You were surprised when Jack led you back to the hotel much earlier than you expected, having just finished lunch and bundling back up in your coats to brave the increasing snow.

You weren't complaining though, as you entered the lobby just as the snow had started to become a blizzard, more than happy to escape the cold for the rest of the day. 

You were taken back to your room, and perhaps a little disappointed as you entered the bedroom, finding no gifts laid out. 

Jack took notice, chuckling and kissing your cheek.

“ _ Later _ Honey, we’re only stopping by to get rid of our winter gear,” he said warmly, shedding his coat once more and changing into some comfortable lounging clothes. He encouraged you to do the same, so quickly you dressed into a large baggy sweater dress, warm leggings and soft ugg boots. He took your hand once you were ready, and just as quickly as you had arrived to your suite, you were swept away to some unknown part of the hotel. 

  
  


* * *

You were  _ delighted _ when you passed through two large glass doors to what you could only describe as a mini spa resort. 

The air was warm and misty, smelling vaguely of vanilla and pine, tiled floors made shoes click as they passed over it, the walls were gray, with a large mural walk behind the tall reception desk. The hotel's logo stood out on the mural of trees, and sitting underneath, behind the desk were two petite young women who greeted you with a smile. 

“Mr Daniels?” one of them asked in a strong italian accent. 

Jack smiled and nodded, pulling you with him as you were led down a short hallway to the side, and then into a changing room where robes and towels waited for you. 

You both undressed in your cubicles, putting on the towels and plush white robes provided for you. Jack took your hand back once the two of you were ready for whatever treatment you were about to get. 

As usual, Jack had spared no expense, and the two of you were treated to a full spa experience. Jack had even gone the extra mile to give you a full beauty treatment as an added bonus. 

You were able to relax in the Sauna together, your head resting on Jack’s shoulder as the heat sweat away your stresses. That was followed up by your beauty treatment. Mani and pedi, facial, exfoliation, face mask, eye mask, you experienced the full works, all while Jack cooled off in an Ice bath.

You enjoyed your pedicure along with a small sample of fruits and sandwich , followed up with a delicious slice of decadent cake, and a glass of champagne. 

And the entire spa experience was topped off with a couples massage. 

Jack reached across the small gap between your tables whenever he could to hold your hand in his. Any tension you had in your body melted away thanks to the expert hands of your masseuse and the scented oils coating your skin. 

Sighing, you closed your eyes, trying hard not to fall asleep due to your extremely relaxed state, waiting to enjoy the feeling as much as possible by not drifting off. 

You giggled, along with your masseuses when Jack's steady snore revibriated along the tiled walls, his hand relaxing in your grip as he drifted off, completely and utterly relaxed.

* * *

By the time your massage had ended you were feeling more loose and relaxed than you had ever felt in your life, you rolled your shoulders with a content sigh, loving how loose your muscles felt. 

“Damn Darlin, I didn't even realize my back was hurting so much until the pain went away,” Jack sighed beside you, taking your hand as you made your way back to the changing room to shower off the oil still coated to your skin. 

“You enjoy your beauty treatment?” he asked, taking your hand in his once you were dressed, inspecting your manicure and affectionately stroking your fingers with his. 

“Yes,” you nodded smiling at him. “Thank you.” 

He smiled back and kissed your forehead. “Not that you _ need _ a beauty treatment Darlin, you’re already stunning,” he said, making you blush. 

Washed, dried, and dressed you made your way back to your suite together. 

* * *

As he had promised earlier, gifts were now laid out on the bed, you bounced over to them excitedly, making Jack chuckle at your eagerness. Three boxes, with no clothes set out that evening, which surprised and intrigued you. As expected, one of the boxes contained a lingerie set, red and lacy, but unlike the other set the had bought for you so far, they were not intended to be practical, usable underwear as well, as the cups of the ‘bra’ were not there, the lace would perfectly frame your breasts, leaving them exposed for Jacks viewing pleasure. The ‘panties’ were matching, crotchless, this set was purely to wrap you up nice and pretty leaving everything open to Jack so he would not have to remove a single piece from you to get what he wants. 

He growled softly behind you, wrapping his arms around you to kiss at your neck. “Gonna look so good in that Darlin,” he said, voice deep with lust already at the thought of you wearing it. 

“Open the others” 

You placed the first box down back on the bed, reaching for the next closest box and lifting the lid. Instantly you felt yourself growing wet at the sight of its content. 

“I hope after last night you won't be too sore to play with these tonight,” Jack’s teasing voice tickled your neck as you stared down at the toys in the box. 

So far, in the short time you had been together you had experimented with toys only a handful of times, and so far, they had been simple bullets and vibes. Evidently tonight, Jack wanted to be a bit more,  _ experimental.  _

One simple, silver bullet vibe, a finger vibe, a silicone egg attached to a silicone string you could only guess vibrated, and the largest dildo you had ever seen in person. Your heart was beating fast in anticipation, and you were sure Jack could feel it with his lips latched to your pulse point. 

“Open the last one,” he rasped.

You almost dropped the box as you opened it, overwhelming anticipation making you shake as you stared down at a toy you had only ever dreamed about being used on you. 

Nipple and clit pumps, you were certain Jack was planning on a night just as intense as the last night, and you were more than looking forward to it. 

“Go, get changed, I’ll be waiting for you.” 

You were quick to change in the ensuite, touching up your hair in the mirror and re-applying Jacks favorite mascara. When you came back out to the bedroom, dressed in the exposing red number, Jack was laid out on the bed, even more exposed than you, completely nude as he lay back with a cocky grin, slowly pumping his hardening cock. 

You feigned feeling bashful, hiding half of your body behind the door frame and avoiding his eyes. He chuckled, becoming you over with his finger. 

“No need to feel shy Darlin, you look good enough to eat,” he hummed, still stroking his cock slowly with one hand while the other was open to you in invitation. You padded over the soft carpet, still pretending to feel shy. As soon as you were in reach he pulled you to the bed, pushing you onto your back and bending over you to give you a kiss. 

“I really could eat you up, you sexy little thing,” he teased, his fingers dancing across your skin to the lacy edges of your ‘bra’, the pads of his fingers brushing against your bare breasts as he played with the lace. 

“These,” he said, squeezing your breasts, weighing them in his palm. “A meal fit for a king,” he continued, growling before dipping his head further to mouth at your breasts. He lavished attention to them, making sure to toy with the one not currently in his mouth with his hand, squeezing, kneading the flesh in his large calloused hands, and tweaking your nipple while he licked and suckled on the other one. 

You moaned, already aroused just by looking at the toys he had selected for that night, but even further so now. You felt your arousal leak out of you, with no barrier to hold it thanks to the lack of material covering your centre. 

Jack switched, making sure each of your breasts felt the attention of his mouth, you looked down at him, and found him staring back at you with intense, dark eyes, watching your every reaction, every gasp and moan. 

“Fuck, I love your tits,” he moaned agaisnt your skin, placing a few soft kisses to your peaked nipples before pulling away. His hand stroking the flesh of your thigh as he sat up, erection proudly twitching against his stomach. 

“Which of those toys caught your attention most, baby?” He asked, positioning you gently further back on the bed. 

“T-the pumps,” you answered truthfully, rubbing your coated thighs together in anticipation as Jack got up off the bed to collect the boxes. 

“Yeah? You want Daddy to torture your nipples and poor little clit?” he asked, setting the boxes beside you on the bed. 

You nodded up at him eagerly. 

“Daddy will do just that,” he promised, picking out the finger vibe from the box and sliding it over his index, switching it on so it buzzed lightly. “But I want to try them all out on you baby.” 

His finger started at your nipples, trailing slowly down your body until he reached your clit, circling it gently so the vibrations barely tickled you. You whined, lifting your hips , trying to gain more pressure to your clit, but Jack slapped your thich in warning. 

“You take what Daddy gives you,” he reminded you, torturing you further by rubbing his vibrating finger over your clit directly, so lightly you could only just feel the promise of the vibrations against your swollen bud. 

“Daddy _ please _ ,” you whined, pouting when he chuckled at you, not taking pity on you. 

“Patience is a virtue sugar,” he teased, leaning over to rasp in your ear. “Daddy will will make you cum so hard so much it fucking _ hurts _ if you be good for me.”

You moaned, knowing full well Jack always kept his promises if you behaved for him. 

“Imagine that big one inside you,” he continued, knowing full well his words could turn you on just as much as his touches. “I wanna see your sweet little peach of a pussy stretch around that, your hungry little hole taking that massive cock, fuck, I bet it would hurt to cum around that thing, your cunt stretched so much and tightening around that, fuck  _ I  _ could cum just _ imagining _ that.” 

You moaned again, nodding your head and silently begging for just that, wanting to please him, wanting that painful pleasure. 

Your eyes were closed, imagining his little fantasy, how good it would feel when he surprised you by pushing the vibe right onto your clit, making you yelp. 

“We’re gonna start small, and make our way up,” he said, sitting back up to watch you writhe under the pleasure of the vibe. “It’s going to be another long night Baby girl.” 

* * *

Jack had successfully made you cum with the finger vibe without ever sliding anything inside you, and had slowly worked you open with the small silver vibe, pumping it in and out of you slowly, bringing you back to the edge of pleasure before abandoning it to the side. You whined in frustration as he took his sweet time picking the next toy, much to your annoyance. There were two toys left in that box and you knew he was going to end with the larger one. He was simply trying to rile you up. 

Deciding you were being just a bit too bratty with your complaints, he gave your pussy a harsh slap.

“Patience Baby,” he warned with a growl. “That's your second warning!” 

You bit your lip, trying to silence yourself as he pretended to decide which toy to use. 

Eventually he picks up the silicone egg and returned to his previous position between your legs, laying on his stomach so he could watch up close. 

He turned the egg on, feeling it buzz in his palm before slowly pushing it inside you, cooing gently about how good your pussy looked, framed by your panties as it stretched around the widest part of the egg. Shoving it inside you as deep as it could reach he watched with fascination how slick leaked from you with each powerful buzz. 

“Remember, you can’t cum until Daddy says you can,” he laughed before licking up your arousal with a moan. You heard him whisper against your folds how you tasted so good. 

You were focusing hard on not cumming until he said so, but that was made far more difficult when he took a hold of the silicone ‘string’ attached to the toy, slowly pulling it down your channel and stretching your hole again. 

You keened, arching your back and trying so hard to wait for his permission. He repeated the action, pushing the vibrating egg deep inside you before slowly pulling it out, stopping when you stretched around the widest point. He watched entranced, growling hungrily every time your entrance stretched around it. 

He kissed your clit, circling his tongue around it, drinking up your moans. 

“Fuck baby, watching my sweet little cunt stretch like this, just makes me want to see what else I can fit in you,” he moaned, lapping up at your folds now. “Im gonna buy the _ biggest _ fucking toy I can find when we get home, we’re gonna find your limit one day.” 

His lips latched onto your core, eating you out vigorously, and still playing with the toy with his hand, he was struggling to grip it securely with how much you were leaking. 

He shoved the toy back inside, pushing up right against your g-spot as he began suckling your clit. 

You shrieked, trying not to wriggle too much as you begged, helplessly, for permission. 

“Daddy! Please! Please!  _ Pleasepleaseplease _ !” You wailed. Looking down at him, between your legs, eyes watching you intently again, you saw him nod. 

_ Permission.  _

You thanked him with a cry as you arched further off of the bed, pushing your hips up into his mouth as he drank down your release, tongue lapping at your hole beside the silicone still hanging out of you. You clenched down around the toy, shaking as your walls contracted around the vibrations. 

“Daddy!” You whined, slowly rocking your hips into his face as you rode out your orgasm. As the waves of pleasure washed away, Jack ever so slowly pulled the toy out of you, kissing your clit in praise as he did so. You whimpered, sensitive as he kissed you there. 

He cooed again as you stretched around the toy, watching as he pulled it out at a snails pace, enraptured at the sight. 

“My pretty little pussy,” he praised, diving to lap up at you again once the toy popped out of you. You mewled, lazily trying to push him away, but he wouldn't be denied his sweet treat. 

Jack tossed the toy to the side and crawled up your body, lifting your thighs around his waist. Teasingly, he rocked his hips so his cock, now leaking pre-cum onto your skin.

“Daddy wants to be inside his pretty little pussy,” he rasped. “I know you’re sensitive baby,  _ oohhh _ but daddy wants to make you a creamy mess before you take that big one, I need you slick with both our cum before I stretch you out with that thing.” 

He was rambling, but watched your expression carefully as he lined himself up with your hole, smearing his pre-cum around your folds, waiting for any kind of refusal before pushing his hips forward and filling you easily thanks to his attentions with the egg. 

“Fuck, there we go,” he groaned when the flesh of your ass met his thighs. Bottoming out inside of you. You moaned loudly as he filled you up, feeling his tip meet your innermost wall. “I aint ever been in a pussy this good Baby.”

Having neglected his cock for so long, choosing to pleasure you ahead of himself, Jack didn’t bother wasting time building up a slow and steady pace. He pounded into you hard and fast as he always did when chasing his own release and slaps echoing in the room. 

He crashed his lips on yours, noses bumping together as the taste of your cum flooded your mouth. The kiss was sloppy, and messy, but Jack desperately seemed to need his mouth on yours as his hips rammed yours. You could tell by his desperation he would not last long, he rarely did when he had aroused himself so much by pleasuring you.

Once, twice, three times he bucked into you hard before warm cum flooded your insides, he pulled your bottom lip into his mouth and bit hard, but not hard enough to draw blood, groaning loudly. 

You didn’t complain about the fact that he had sought his own release as he lazily pulled out of you, pushing his seed back inside you with his thumb, knowing full well he intended to make you cum at least once more that night. 

“Baby,” he sighed, licking his thumb clean of your combined releases. “What's your color? You still good to try take that big one?”

“Green Daddy,” you sighed, settling into the pillows comfortably, preparing yourself for the challenge. 

“My perfect girl,” he said proudly, kissing your cheek and retrieving the toy. 

You knew there were larger toys out there, but this would be the largest you had ever taken personally, it was bigger than Jack, who was already an impressive size himself. He placed the toy beside you on the bed before opening the bedside drawer for a bottle of lube.

“I know you’re wet Darlin, you’re always wet for me, your horny little cunt’s always up for more, isn’t she? But we still need to prep you” he said, coating his fingers in lube and putting two in you straight away. The artificial lube, mixed with both of your cum made obscene noises as Jack pumped his fingers and stretched you open. 

“Daddy can get hard again on that noise alone Honey Bee,” he chuckled, laughing harder as your eyes widened as you glanced down at his spent, wet cock that was already twitching with interest. 

You bit your lip and wiggled slightly, stopping when his eyes cut back to your face in warning. 

“Are you going to take me again Daddy?” You asked as a third finger pushed inside you. 

“Ohhh, you can bet on it Baby,” he moaned, watching your hole stretching around his fingers. When he managed to fit a fourth, large finger inside you, he stretched you wide open so he could stare into your hole, groaning at the sight. 

“My perfect little cunt,” he whispered before spitting into your hole, giving you an obnoxiously cocky grin before pulling his fingers free and shoving them in your mouth to clean. 

Obediently you lapped them up, cleaning your combined cum and lube off of his fingers while his free hand opened the bottle again. Once he deemed his fingers acceptably clean he pulled them out of the hot cavern of your mouth and picked up the toy, coating it generously in lube. 

“You sweet little pussy’s gonna look so good taking this,” he growled, shoving your legs apart as wide as they could go and lining the tip of the toy up at your entrance. He was extremely careful, as he pushed it forward, watching your reaction carefully for any sign of discomfort. Even with the stretching and copious slick from the lube and cum it was a struggle to take, the stretch was burning and so far he had only pushed the tip in. Jack paused, waiting patiently for your face to relax as he slowly pulled the toy out, then back in, pushing just a little bit deeper each time, pausing, waiting for you to adjust each time you grimmanced. 

It took a lot of hard work, but with both your efforts the toy was eventually pushed as deep as it could go. You both moaned in unison once the toy could go no deeper. Jack laid down on his stomach, between your legs, staring longingly once again at the stretch of your pussy. 

“Baby,” he cooed in adoration, running this finger around the toy where your hole stretched around it, making you whimper. “Look at that,  _ fuck _ , just imagine how much we could get to fit in you with practice. Your sweet, tiny little pussy’s stretched so wide, Can’t wait to make you cum on that, bet it’s gonna hurt, make you cry, sweet thing.” 

You were stretched so wide that the arousal you felt at his words could not escape, simply filling you up further, making you whine. 

“Wait here, hold your legs open,” he ordered getting up off the bed, you noticed he was hard again already, having worked himself up watching you stretch around the new toy. 

He picked up the last box.

_ Oh. _

You had forgotten about that.

Jack gently picked up the pumps before returning to you, gently attaching the suction cups to each nipple and your clit. He loved how your breasts look, framed by the ‘bra’, pump attached to your nipples. 

“Gonna make you cum so hard, it’ll hurt _ so good _ baby,” he rasped, voice deep and gravely with lust. 

He squeezed the pump gently in one hand, watching how you would react with fierce intensity and hunger. The first pump was just enough to feel a slight suction, a mild sensation, but he continued to pump away slowly, watching the way your nipples began pulling up into the clear cups. He groaned at the sight, and once your nipples and clit started to feel the tight suction you whined loudly in both pain and pleasure, unintentionally squeezing around the large toy inside you still. 

Without warning Jack repeatedly squeezed the pump hard and fast, startling you with the sudden, constant suction.

“Ahhhh! Daddy!” You yelped, struggling to keep still for him.

“You know your words,” he reminded you. “They’re there if you need them.” 

You shook your head no, wanting that painful orgasm he promised you and was intent on giving you. 

You were sobbing as he pumped away, clit and nipples red and raw as they were pulled up into the cups, there would be marks in the morning, no doubt about that. 

It was painful, but incredibly arousing at the same time, they had never been this sensitive before, this abused and your head was swimming in the delirium of it. 

Jack jerked himself off with his free hand above you, as you squirmed beneath him, the painful, burning stretch of the toy, and the constant and the arduous suction on your most sensitive parts were driving you insane. 

To torment you further, Jack placed the pump down but did not release the suction, instead, grabbing onto one of the cups on your nipples and tugging at it. You cried, the pain agonising but it just made you anticipate your orgasm all the more. 

Proud of the reaction he pulled from you, his hand moved to the suction cup on your clit, repeating the action. You shrieked, louder than you ever had before and Jack abandoned his cock to cover your mouth, as he repeatedly tugged at the cup, muffling your shrieks. 

“Normally I love your noises Baby but we don't need people coming to investigate that now do we?” he teased. “Now I'm going to let go and you’re going to cum for me. You understand?”

You nodded into his hand. 

“Good, you need to scream like that, do it into the pillow,” he said before pulling his hand from your mouth to grip the toy filling you up by the base and jackhammering it inside of you, still tugging at the pump on your clit. 

It was instantaneous, and as painful as he had promised. Your hole was stretched as wide as it could possibly go right now and gripping hard on the toy that was stuffed inside you. Jack growled, watching with rapt fascination as your poor abused hole rhythmically clenched around the artificial cock. 

You didn't shake as much as you thrashed, pulling the pillow to your face to scream your voice hoarse as tears escaped your eyes due to the pain you were drunk on. 

Wet squelching, screams and Jack’s praises and curses filled the room as you came and cum gushed from you. Your body was both trying to milk the toy and push it out of you at the same time, and you realized the toy was being forced from you because you were squirting around it. Jack seemed unaware given how big the toy was, but he was preparing to enter you the second he pulled the toy from you, the hand previously tugging at your clit pump was stroking his cock while the hand still on the toy quickly pulled it out of you, coating him in the cum still squirting from you. 

“ _ Fuck Baby _ !” he shouted, surprised for just a moment before he growled and quickly shoved himself in your gaping pussy before you finished. Pounding into you at a brutal pace, unintentionally but happily massaging that spot making you squirt, drenching his front in even more cum before your body could take no more.

“Fuck I didn’t think this would be how I made you squirt the first time, but I'm not complaining,” he groaned in your ear, ripping your pillow away from your face and pounding into you, holding your still thrashing body tightly to him, ignoring the pump still on you as his cock destroyed your hole. Over and over again.

His pace was brutal and you cried, from the intense pain and pleasure of your orgasm, from the suction still on your nipples and clit, from the overstimulation of him pounding into you before you had even finished, how tender and swollen your sex was that was continuing to be abused, and the words that dripped from his mouth. 

“ _ My _ fucking pussy, this is  _ mine _ ,” he growled, his voice sounding feral and animalistic. “No ones ever going to please you the way I do, fill you the way I do, every inch of you is mine!” 

_ “Y-yours, _ ” you eeped out, voice faint after screaming so loud. 

That was all he needed to push him over the edge, shouting his release as he pulled you up into him and he pushed in as deep as he could go, ignoring how the pump dug into both of you, hitting your cervix, making you cry out as he came.You felt it leak out of you, your abused hole unable to hold it in as he pulled out. Pausing a moment to free you of the pump, making you hiss in pain and relief before Jack collapsed on top of you with a groan, resting his head between your breasts and wrapping his arms around you. 

You weren't sure how long the two of you lay there, clinging to each other, hearts and breath slowing down and sweat cooling from your skin as you stroked his hair. 

Eventually, once he was no longer panting, Jack sat up, hair clinging to his sweaty forehead as he took survey of the mess on yourselves and the bed. 

“You good baby?” he asked, the need for sleep clinging to his voice. 

“Yeah,” you whispered. “That was…”

“Intense?” he supplied with a weak chuckle, getting up off of the bed. “Come on baby, let clean up and get you sorted.” 

You whined in complaint, rolling to your side, back to him. 

“I know you’re tired,” he cooed, gently picking you up and carrying you to the ensuite. “But you’ll regret waking up in a wet bed, covered in cum and sore as all hell.” 

“Fine” you sighed, wrapping your arms around his neck, more than happy to let him do all the work, and you knew he was more than happy to do it. 

He took extra care with you that night, cleaning you up, removing the lingerie from your body, soothing your sore abused nipples with ointment, changing the bedsheets and praising you as you snuggled to him every chance you got. 

You were already asleep by the time he put you to bed and tucked you in beside him.

  
  
  



End file.
